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Wikipedia

Glucose

August 26, 2023

Glucose is a sugar with the molecular formula C6H12O6. Glucose is overall the most abundant monosaccharide,[3] a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight, where it is used to make cellulose in cell walls, the most abundant carbohydrate in the world.[4]

d-Glucose

Skeletal formula of d-glucose

Haworth projection of α-d-glucopyranose

Fischer projection of d-glucose
Names
Pronunciation /ˈɡluːkoʊz/, /ɡluːkoʊs/
IUPAC name
  • Systematic name:
    • (2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanal
  • Allowed trivial names:
    • ᴅ-Glucose
    • ᴅ-gluco-Hexose
Preferred IUPAC name
PINs are not identified for natural products.
Systematic IUPAC name
(3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol (cyclic)
Other names
  • Blood sugars
  • Dextrose
  • Corn sugar
  • d-Glucose
  • Grape sugar
Identifiers
  • 50-99-7 Y
  • 492-62-6 (α-d-glucopyranose) Y
3D model (JSmol)
  • Interactive image
  • Interactive image
3DMet
  • B01203
Abbreviations Glc
1281604
ChEBI
  • CHEBI:4167 Y
ChEMBL
  • ChEMBL1222250 Y
ChemSpider
  • 5589 Y
EC Number
  • 200-075-1
83256
  • 4536
KEGG
  • C00031 Y
MeSH Glucose
  • 5793
RTECS number
  • LZ6600000
UNII
  • 5SL0G7R0OK Y
  • 5J5I9EB41E (α-d-glucopyranose) Y
  • InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6?/m1/s1 Y
    Key: WQZGKKKJIJFFOK-GASJEMHNSA-N Y
  • OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O
  • C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O
Properties
C6H12O6
Molar mass 180.156 g/mol
Appearance White powder
Density 1.54 g/cm3
Melting point α-d-Glucose: 146 °C (295 °F; 419 K) β-d-Glucose: 150 °C (302 °F; 423 K)
909 g/L (25 °C (77 °F))
−101.5×10−6 cm3/mol
8.6827
Thermochemistry
218.6 J/(K·mol)[1]
209.2 J/(K·mol)[1]
−1271 kJ/mol[2]
2,805 kJ/mol (670 kcal/mol)
Pharmacology
B05CX01 (WHO) V04CA02 (WHO), V06DC01 (WHO)
Hazards
NFPA 704 (fire diamond)
Health 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
1
0
Safety data sheet (SDS) ICSC 08655
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

In energy metabolism, glucose is the most important source of energy in all organisms. Glucose for metabolism is stored as a polymer, in plants mainly as starch and amylopectin, and in animals as glycogen. Glucose circulates in the blood of animals as blood sugar. The naturally occurring form of glucose is d-glucose, while its stereoisomer l-glucose is produced synthetically in comparatively small amounts and is less biologically active.[5] Glucose is a monosaccharide containing six carbon atoms and an aldehyde group, and is therefore an aldohexose. The glucose molecule can exist in an open-chain (acyclic) as well as ring (cyclic) form. Glucose is naturally occurring and is found in its free state in fruits and other parts of plants. In animals, glucose is released from the breakdown of glycogen in a process known as glycogenolysis.

Glucose, as intravenous sugar solution, is on the World Health Organization's List of Essential Medicines.[6] It is also on the list in combination with sodium chloride.[6]

The name glucose is derived from Ancient Greek γλεῦκος (gleûkos, "wine, must"), from γλυκύς (glykýs, "sweet").[7][8] The suffix "-ose" is a chemical classifier, denoting a sugar.

History Edit

Glucose was first isolated from raisins in 1747 by the German chemist Andreas Marggraf.[9][10] Glucose was discovered in grapes by another German chemist – Johann Tobias Lowitz – in 1792, and distinguished as being different from cane sugar (sucrose). Glucose is the term coined by Jean Baptiste Dumas in 1838, which has prevailed in the chemical literature. Friedrich August Kekulé proposed the term dextrose (from the Latin dexter, meaning "right"), because in aqueous solution of glucose, the plane of linearly polarized light is turned to the right. In contrast, l-fructose (a ketohexose) and l-glucose turn linearly polarized light to the left. The earlier notation according to the rotation of the plane of linearly polarized light (d and l-nomenclature) was later abandoned in favor of the d- and l-notation, which refers to the absolute configuration of the asymmetric center farthest from the carbonyl group, and in concordance with the configuration of d- or l-glyceraldehyde.[11][12]

Since glucose is a basic necessity of many organisms, a correct understanding of its chemical makeup and structure contributed greatly to a general advancement in organic chemistry. This understanding occurred largely as a result of the investigations of Emil Fischer, a German chemist who received the 1902 Nobel Prize in Chemistry for his findings.[13] The synthesis of glucose established the structure of organic material and consequently formed the first definitive validation of Jacobus Henricus van 't Hoff's theories of chemical kinetics and the arrangements of chemical bonds in carbon-bearing molecules.[14] Between 1891 and 1894, Fischer established the stereochemical configuration of all the known sugars and correctly predicted the possible isomers, applying Van 't Hoff's theory of asymmetrical carbon atoms. The names initially referred to the natural substances. Their enantiomers were given the same name with the introduction of systematic nomenclatures, taking into account absolute stereochemistry (e.g. Fischer nomenclature, d/l nomenclature).

For the discovery of the metabolism of glucose Otto Meyerhof received the Nobel Prize in Physiology or Medicine in 1922.[15] Hans von Euler-Chelpin was awarded the Nobel Prize in Chemistry along with Arthur Harden in 1929 for their "research on the fermentation of sugar and their share of enzymes in this process".[16][17] In 1947, Bernardo Houssay (for his discovery of the role of the pituitary gland in the metabolism of glucose and the derived carbohydrates) as well as Carl and Gerty Cori (for their discovery of the conversion of glycogen from glucose) received the Nobel Prize in Physiology or Medicine.[18][19][20] In 1970, Luis Leloir was awarded the Nobel Prize in Chemistry for the discovery of glucose-derived sugar nucleotides in the biosynthesis of carbohydrates.[21]

Chemical and physical properties Edit

Glucose forms white or colorless solids that are highly soluble in water and acetic acid but poorly soluble in methanol and ethanol. They melt at 146 °C (295 °F) (α) and 150 °C (302 °F) (β), and decompose starting at 188 °C (370 °F) with release of various volatile products, ultimately leaving a residue of carbon.[22] Glucose has a pK value of 12.16 at 25 °C (77 °F) in water.[23]

With six carbon atoms, it is classed as a hexose, a subcategory of the monosaccharides. d-Glucose is one of the sixteen aldohexose stereoisomers. The d-isomer, d-glucose, also known as dextrose, occurs widely in nature, but the l-isomer, l-glucose, does not. Glucose can be obtained by hydrolysis of carbohydrates such as milk sugar (lactose), cane sugar (sucrose), maltose, cellulose, glycogen, etc. Dextrose is commonly commercially manufactured from cornstarch in the US and Japan, from potato and wheat starch in Europe, and from tapioca starch in tropical areas.[24] The manufacturing process uses hydrolysis via pressurized steaming at controlled pH in a jet followed by further enzymatic depolymerization.[25] Unbonded glucose is one of the main ingredients of honey.

Structure and nomenclature Edit

See also: Mutarotation
 
Mutarotation of glucose

Glucose is usually present in solid form as a monohydrate with a closed pyran ring (dextrose hydrate). In aqueous solution, on the other hand, it is an open-chain to a small extent and is present predominantly as α- or β-pyranose, which interconvert. From aqueous solutions, the three known forms can be crystallized: α-glucopyranose, β-glucopyranose and β-glucopyranose hydrate.[26] Glucose is a building block of the disaccharides lactose and sucrose (cane or beet sugar), of oligosaccharides such as raffinose and of polysaccharides such as starch, amylopectin, glycogen, and cellulose. The glass transition temperature of glucose is 31 °C (88 °F) and the Gordon–Taylor constant (an experimentally determined constant for the prediction of the glass transition temperature for different mass fractions of a mixture of two substances)[27] is 4.5.[28]

Forms and projections of d-glucose in comparison
Natta projection Haworth projection
   
α-d-glucofuranose 		 
β-d-glucofuranose
 
α-d-glucopyranose 		 
β-d-glucopyranose
α-d-Glucopyranose in (1) Tollens/Fischer (2) Haworth projection (3) chair conformation (4) Mills projection
 

Open-chain form Edit

 
Glucose can exist in both a straight-chain and ring form.

The open-chain form of glucose makes up less than 0.02% of the glucose molecules in an aqueous solution at equilibrium.[29] The rest is one of two cyclic hemiacetal forms. In its open-chain form, the glucose molecule has an open (as opposed to cyclic) unbranched backbone of six carbon atoms, where C-1 is part of an aldehyde group H(C=O)−. Therefore, glucose is also classified as an aldose, or an aldohexose. The aldehyde group makes glucose a reducing sugar giving a positive reaction with the Fehling test.

Cyclic forms Edit

Cyclic forms of glucose
 
 
 
 
 
 
 
 
From left to right: Haworth projections and ball-and-stick structures of the α- and β- anomers of D-glucopyranose (top row) and D-glucofuranose (bottom row)

In solutions, the open-chain form of glucose (either "D-" or "L-") exists in equilibrium with several cyclic isomers, each containing a ring of carbons closed by one oxygen atom. In aqueous solution, however, more than 99% of glucose molecules exist as pyranose forms. The open-chain form is limited to about 0.25%, and furanose forms exist in negligible amounts. The terms "glucose" and "D-glucose" are generally used for these cyclic forms as well. The ring arises from the open-chain form by an intramolecular nucleophilic addition reaction between the aldehyde group (at C-1) and either the C-4 or C-5 hydroxyl group, forming a hemiacetal linkage, −C(OH)H−O−.

The reaction between C-1 and C-5 yields a six-membered heterocyclic system called a pyranose, which is a monosaccharide sugar (hence "-ose") containing a derivatised pyran skeleton. The (much rarer) reaction between C-1 and C-4 yields a five-membered furanose ring, named after the cyclic ether furan. In either case, each carbon in the ring has one hydrogen and one hydroxyl attached, except for the last carbon (C-4 or C-5) where the hydroxyl is replaced by the remainder of the open molecule (which is −(C(CH2OH)HOH)−H or −(CHOH)−H respectively).

The ring-closing reaction can give two products, denoted "α-" and "β-". When a glucopyranose molecule is drawn in the Haworth projection, the designation "α-" means that the hydroxyl group attached to C-1 and the −CH2OH group at C-5 lies on opposite sides of the ring's plane (a trans arrangement), while "β-" means that they are on the same side of the plane (a cis arrangement). Therefore, the open-chain isomer D-glucose gives rise to four distinct cyclic isomers: α-D-glucopyranose, β-D-glucopyranose, α-D-glucofuranose, and β-D-glucofuranose. These five structures exist in equilibrium and interconvert, and the interconversion is much more rapid with acid catalysis.

 
Widely proposed arrow-pushing mechanism for acid-catalyzed dynamic equilibrium between the α- and β- anomers of D-glucopyranose
 
 
Chair conformations of α- (left) and β- (right) D-glucopyranose

The other open-chain isomer L-glucose similarly gives rise to four distinct cyclic forms of L-glucose, each the mirror image of the corresponding D-glucose.

The glucopyranose ring (α or β) can assume several non-planar shapes, analogous to the "chair" and "boat" conformations of cyclohexane. Similarly, the glucofuranose ring may assume several shapes, analogous to the "envelope" conformations of cyclopentane.

In the solid state, only the glucopyranose forms are observed.

Some derivatives of glucofuranose, such as 1,2-O-isopropylidene-D-glucofuranose are stable and can be obtained pure as crystalline solids.[30][31] For example, reaction of α-D-glucose with para-tolylboronic acid H3C−(C6H4)−B(OH)2 reforms the normal pyranose ring to yield the 4-fold ester α-D-glucofuranose-1,2:3,5-bis(p-tolylboronate).[32]

Mutarotation Edit

 
Mutarotation: d-glucose molecules exist as cyclic hemiacetals that are epimeric (= diastereomeric) to each other. The epimeric ratio α:β is 36:64. In the α-D-glucopyranose (left), the blue-labelled hydroxy group is in the axial position at the anomeric centre, whereas in the β-D-glucopyranose (right) the blue-labelled hydroxy group is in equatorial position at the anomeric centre.

Mutarotation consists of a temporary reversal of the ring-forming reaction, resulting in the open-chain form, followed by a reforming of the ring. The ring closure step may use a different −OH group than the one recreated by the opening step (thus switching between pyranose and furanose forms), or the new hemiacetal group created on C-1 may have the same or opposite handedness as the original one (thus switching between the α and β forms). Thus, though the open-chain form is barely detectable in solution, it is an essential component of the equilibrium.

The open-chain form is thermodynamically unstable, and it spontaneously isomerizes to the cyclic forms. (Although the ring closure reaction could in theory create four- or three-atom rings, these would be highly strained, and are not observed in practice.) In solutions at room temperature, the four cyclic isomers interconvert over a time scale of hours, in a process called mutarotation.[33] Starting from any proportions, the mixture converges to a stable ratio of α:β 36:64. The ratio would be α:β 11:89 if it were not for the influence of the anomeric effect.[34] Mutarotation is considerably slower at temperatures close to 0 °C (32 °F).

Optical activity Edit

Whether in water or the solid form, d-(+)-glucose is dextrorotatory, meaning it will rotate the direction of polarized light clockwise as seen looking toward the light source. The effect is due to the chirality of the molecules, and indeed the mirror-image isomer, l-(−)-glucose, is levorotatory (rotates polarized light counterclockwise) by the same amount. The strength of the effect is different for each of the five tautomers.

Note that the d- prefix does not refer directly to the optical properties of the compound. It indicates that the C-5 chiral centre has the same handedness as that of d-glyceraldehyde (which was so labelled because it is dextrorotatory). The fact that d-glucose is dextrorotatory is a combined effect of its four chiral centres, not just of C-5; and indeed some of the other d-aldohexoses are levorotatory.

The conversion between the two anomers can be observed in a polarimeter since pure α-d-glucose has a specific rotation angle of +112.2° mL/(dm·g), pure β-d-glucose of +17.5° mL/(dm·g).[35] When equilibrium has been reached after a certain time due to mutarotation, the angle of rotation is +52.7° mL/(dm·g).[35] By adding acid or base, this transformation is much accelerated. The equilibration takes place via the open-chain aldehyde form.

Isomerisation Edit

In dilute sodium hydroxide or other dilute bases, the monosaccharides mannose, glucose and fructose interconvert (via a Lobry de Bruyn–Alberda–Van Ekenstein transformation), so that a balance between these isomers is formed. This reaction proceeds via an enediol:

 

Biochemical properties Edit

Glucose is the most abundant monosaccharide. Glucose is also the most widely used aldohexose in most living organisms. One possible explanation for this is that glucose has a lower tendency than other aldohexoses to react nonspecifically with the amine groups of proteins.[36] This reaction—glycation—impairs or destroys the function of many proteins,[36] e.g. in glycated hemoglobin. Glucose's low rate of glycation can be attributed to its having a more stable cyclic form compared to other aldohexoses, which means it spends less time than they do in its reactive open-chain form.[36] The reason for glucose having the most stable cyclic form of all the aldohexoses is that its hydroxy groups (with the exception of the hydroxy group on the anomeric carbon of d-glucose) are in the equatorial position. Presumably, glucose is the most abundant natural monosaccharide because it is less glycated with proteins than other monosaccharides.[36][37] Another hypothesis is that glucose, being the only d-aldohexose that has all five hydroxy substituents in the equatorial position in the form of β-d-glucose, is more readily accessible to chemical reactions,[38]: 194, 199  for example, for esterification[39]: 363  or acetal formation.[40] For this reason, d-glucose is also a highly preferred building block in natural polysaccharides (glycans). Polysaccharides that are composed solely of glucose are termed glucans.

Glucose is produced by plants through photosynthesis using sunlight, water and carbon dioxide and can be used by all living organisms as an energy and carbon source. However, most glucose does not occur in its free form, but in the form of its polymers, i.e. lactose, sucrose, starch and others which are energy reserve substances, and cellulose and chitin, which are components of the cell wall in plants or fungi and arthropods, respectively. These polymers, when consumed by animals, fungi and bacteria, are degraded to glucose using enzymes. All animals are also able to produce glucose themselves from certain precursors as the need arises. Neurons, cells of the renal medulla and erythrocytes depend on glucose for their energy production.[41] In adult humans, there is about 18 g (0.63 oz) of glucose,[42] of which about 4 g (0.14 oz) is present in the blood.[43] Approximately 180–220 g (6.3–7.8 oz) of glucose is produced in the liver of an adult in 24 hours.[42]

Many of the long-term complications of diabetes (e.g., blindness, kidney failure, and peripheral neuropathy) are probably due to the glycation of proteins or lipids.[44] In contrast, enzyme-regulated addition of sugars to protein is called glycosylation and is essential for the function of many proteins.[45]

Uptake Edit

Ingested glucose initially binds to the receptor for sweet taste on the tongue in humans. This complex of the proteins T1R2 and T1R3 makes it possible to identify glucose-containing food sources. Glucose mainly comes from food—about 300 g (11 oz) per day is produced by conversion of food,[46] but it is also synthesized from other metabolites in the body's cells. In humans, the breakdown of glucose-containing polysaccharides happens in part already during chewing by means of amylase, which is contained in saliva, as well as by maltase, lactase, and sucrase on the brush border of the small intestine. Glucose is a building block of many carbohydrates and can be split off from them using certain enzymes. Glucosidases, a subgroup of the glycosidases, first catalyze the hydrolysis of long-chain glucose-containing polysaccharides, removing terminal glucose. In turn, disaccharides are mostly degraded by specific glycosidases to glucose. The names of the degrading enzymes are often derived from the particular poly- and disaccharide; inter alia, for the degradation of polysaccharide chains there are amylases (named after amylose, a component of starch), cellulases (named after cellulose), chitinases (named after chitin), and more. Furthermore, for the cleavage of disaccharides, there are maltase, lactase, sucrase, trehalase, and others. In humans, about 70 genes are known that code for glycosidases. They have functions in the digestion and degradation of glycogen, sphingolipids, mucopolysaccharides, and poly(ADP-ribose). Humans do not produce cellulases, chitinases, or trehalases, but the bacteria in the gut microbiota do.

In order to get into or out of cell membranes of cells and membranes of cell compartments, glucose requires special transport proteins from the major facilitator superfamily. In the small intestine (more precisely, in the jejunum),[47] glucose is taken up into the intestinal epithelium with the help of glucose transporters[48] via a secondary active transport mechanism called sodium ion-glucose symport via sodium/glucose cotransporter 1 (SGLT1).[49] Further transfer occurs on the basolateral side of the intestinal epithelial cells via the glucose transporter GLUT2,[49] as well uptake into liver cells, kidney cells, cells of the islets of Langerhans, neurons, astrocytes, and tanycytes.[50] Glucose enters the liver via the portal vein and is stored there as a cellular glycogen.[51] In the liver cell, it is phosphorylated by glucokinase at position 6 to form glucose 6-phosphate, which cannot leave the cell. Glucose 6-phosphatase can convert glucose 6-phosphate back into glucose exclusively in the liver, so the body can maintain a sufficient blood glucose concentration. In other cells, uptake happens by passive transport through one of the 14 GLUT proteins.[49] In the other cell types, phosphorylation occurs through a hexokinase, whereupon glucose can no longer diffuse out of the cell.

The glucose transporter GLUT1 is produced by most cell types and is of particular importance for nerve cells and pancreatic β-cells.[49] GLUT3 is highly expressed in nerve cells.[49] Glucose from the bloodstream is taken up by GLUT4 from muscle cells (of the skeletal muscle[52] and heart muscle) and fat cells.[53] GLUT14 is expressed exclusively in testicles.[54] Excess glucose is broken down and converted into fatty acids, which are stored as triglycerides. In the kidneys, glucose in the urine is absorbed via SGLT1 and SGLT2 in the apical cell membranes and transmitted via GLUT2 in the basolateral cell membranes.[55] About 90% of kidney glucose reabsorption is via SGLT2 and about 3% via SGLT1.[56]

Biosynthesis Edit

Main articles: Gluconeogenesis and Glycogenolysis

In plants and some prokaryotes, glucose is a product of photosynthesis.[57] Glucose is also formed by the breakdown of polymeric forms of glucose like glycogen (in animals and mushrooms) or starch (in plants). The cleavage of glycogen is termed glycogenolysis, the cleavage of starch is called starch degradation.[58]

The metabolic pathway that begins with molecules containing two to four carbon atoms (C) and ends in the glucose molecule containing six carbon atoms is called gluconeogenesis and occurs in all living organisms. The smaller starting materials are the result of other metabolic pathways. Ultimately almost all biomolecules come from the assimilation of carbon dioxide in plants and microbes during photosynthesis.[39]: 359  The free energy of formation of α-d-glucose is 917.2 kilojoules per mole.[39]: 59  In humans, gluconeogenesis occurs in the liver and kidney,[59] but also in other cell types. In the liver about 150 g (5.3 oz) of glycogen are stored, in skeletal muscle about 250 g (8.8 oz).[60] However, the glucose released in muscle cells upon cleavage of the glycogen can not be delivered to the circulation because glucose is phosphorylated by the hexokinase, and a glucose-6-phosphatase is not expressed to remove the phosphate group. Unlike for glucose, there is no transport protein for glucose-6-phosphate. Gluconeogenesis allows the organism to build up glucose from other metabolites, including lactate or certain amino acids, while consuming energy. The renal tubular cells can also produce glucose.

Glucose also can be found outside of living organisms in the ambient environment. Glucose concentrations in the atmosphere are detected via collection of samples by aircraft and are known to vary from location to location. For example, glucose concentrations in atmospheric air from inland China range from 0.8 to 20.1 pg/L, whereas east coastal China glucose concentrations range from 10.3 to 142 pg/L.[61]

Glucose degradation Edit

 
Glucose metabolism and various forms of it in the process.
Glucose-containing compounds and isomeric forms are digested and taken up by the body in the intestines, including starch, glycogen, disaccharides and monosaccharides.
Glucose is stored in mainly the liver and muscles as glycogen. It is distributed and used in tissues as free glucose.
Main articles: Glycolysis and Pentose phosphate pathway

In humans, glucose is metabolized by glycolysis[62] and the pentose phosphate pathway.[63] Glycolysis is used by all living organisms,[38]: 551 [64] with small variations, and all organisms generate energy from the breakdown of monosaccharides.[64] In the further course of the metabolism, it can be completely degraded via oxidative decarboxylation, the citric acid cycle (synonym Krebs cycle) and the respiratory chain to water and carbon dioxide. If there is not enough oxygen available for this, the glucose degradation in animals occurs anaerobic to lactate via lactic acid fermentation and releases much less energy. Muscular lactate enters the liver through the bloodstream in mammals, where gluconeogenesis occurs (Cori cycle). With a high supply of glucose, the metabolite acetyl-CoA from the Krebs cycle can also be used for fatty acid synthesis.[65] Glucose is also used to replenish the body's glycogen stores, which are mainly found in liver and skeletal muscle. These processes are hormonally regulated.

In other living organisms, other forms of fermentation can occur. The bacterium Escherichia coli can grow on nutrient media containing glucose as the sole carbon source.[39]: 59  In some bacteria and, in modified form, also in archaea, glucose is degraded via the Entner-Doudoroff pathway.[66]

Use of glucose as an energy source in cells is by either aerobic respiration, anaerobic respiration, or fermentation. The first step of glycolysis is the phosphorylation of glucose by a hexokinase to form glucose 6-phosphate. The main reason for the immediate phosphorylation of glucose is to prevent its diffusion out of the cell as the charged phosphate group prevents glucose 6-phosphate from easily crossing the cell membrane.[67] Furthermore, addition of the high-energy phosphate group activates glucose for subsequent breakdown in later steps of glycolysis. At physiological conditions, this initial reaction is irreversible.

In anaerobic respiration, one glucose molecule produces a net gain of two ATP molecules (four ATP molecules are produced during glycolysis through substrate-level phosphorylation, but two are required by enzymes used during the process).[68] In aerobic respiration, a molecule of glucose is much more profitable in that a maximum net production of 30 or 32 ATP molecules (depending on the organism) is generated.[69]

Click on genes, proteins and metabolites below to link to respective articles.[§ 1]

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Glycolysis and Gluconeogenesis edit
  1. ^ The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".

Tumor cells often grow comparatively quickly and consume an above-average amount of glucose by glycolysis,[70] which leads to the formation of lactate, the end product of fermentation in mammals, even in the presence of oxygen. This is called the Warburg effect. For the increased uptake of glucose in tumors various SGLT and GLUT are overly produced.[71][72]

In yeast, ethanol is fermented at high glucose concentrations, even in the presence of oxygen (which normally leads to respiration rather than fermentation). This is called the Crabtree effect.

Glucose can also degrade to form carbon dioxide through abiotic means. This has been demonstrated to occur experimentally via oxidation and hydrolysis at 22 °C and a pH of 2.5.[73]

Energy source Edit

 
Diagram showing the possible intermediates in glucose degradation; Metabolic pathways orange: glycolysis, green: Entner-Doudoroff pathway, phosphorylating, yellow: Entner-Doudoroff pathway, non-phosphorylating

Glucose is a ubiquitous fuel in biology. It is used as an energy source in organisms, from bacteria to humans, through either aerobic respiration, anaerobic respiration (in bacteria), or fermentation. Glucose is the human body's key source of energy, through aerobic respiration, providing about 3.75 kilocalories (16 kilojoules) of food energy per gram.[74] Breakdown of carbohydrates (e.g., starch) yields mono- and disaccharides, most of which is glucose. Through glycolysis and later in the reactions of the citric acid cycle and oxidative phosphorylation, glucose is oxidized to eventually form carbon dioxide and water, yielding energy mostly in the form of ATP. The insulin reaction, and other mechanisms, regulate the concentration of glucose in the blood. The physiological caloric value of glucose, depending on the source, is 16.2 kilojoules per gram[75] or 15.7 kJ/g (3.74 kcal/g).[76] The high availability of carbohydrates from plant biomass has led to a variety of methods during evolution, especially in microorganisms, to utilize glucose for energy and carbon storage. Differences exist in which end product can no longer be used for energy production. The presence of individual genes, and their gene products, the enzymes, determine which reactions are possible. The metabolic pathway of glycolysis is used by almost all living beings. An essential difference in the use of glycolysis is the recovery of NADPH as a reductant for anabolism that would otherwise have to be generated indirectly.[77]

Glucose and oxygen supply almost all the energy for the brain,[78] so its availability influences psychological processes. When glucose is low, psychological processes requiring mental effort (e.g., self-control, effortful decision-making) are impaired.[79][80][81][82] In the brain, which is dependent on glucose and oxygen as the major source of energy, the glucose concentration is usually 4 to 6 mM (5 mM equals 90 mg/dL),[42] but decreases to 2 to 3 mM when fasting.[83] Confusion occurs below 1 mM and coma at lower levels.[83]

The glucose in the blood is called blood sugar. Blood sugar levels are regulated by glucose-binding nerve cells in the hypothalamus.[84] In addition, glucose in the brain binds to glucose receptors of the reward system in the nucleus accumbens.[84] The binding of glucose to the sweet receptor on the tongue induces a release of various hormones of energy metabolism, either through glucose or through other sugars, leading to an increased cellular uptake and lower blood sugar levels.[85] Artificial sweeteners do not lower blood sugar levels.[85]

The blood sugar content of a healthy person in the short-time fasting state, e.g. after overnight fasting, is about 70 to 100 mg/dL of blood (4 to 5.5 mM). In blood plasma, the measured values are about 10–15% higher. In addition, the values in the arterial blood are higher than the concentrations in the venous blood since glucose is absorbed into the tissue during the passage of the capillary bed. Also in the capillary blood, which is often used for blood sugar determination, the values are sometimes higher than in the venous blood. The glucose content of the blood is regulated by the hormones insulin, incretin and glucagon.[84][86] Insulin lowers the glucose level, glucagon increases it.[42] Furthermore, the hormones adrenaline, thyroxine, glucocorticoids, somatotropin and adrenocorticotropin lead to an increase in the glucose level.[42] There is also a hormone-independent regulation, which is referred to as glucose autoregulation.[87] After food intake the blood sugar concentration increases. Values over 180 mg/dL in venous whole blood are pathological and are termed hyperglycemia, values below 40 mg/dL are termed hypoglycaemia.[88] When needed, glucose is released into the bloodstream by glucose-6-phosphatase from glucose-6-phosphate originating from liver and kidney glycogen, thereby regulating the homeostasis of blood glucose concentration.[59][41] In ruminants, the blood glucose concentration is lower (60 mg/dL in cattle and 40 mg/dL in sheep), because the carbohydrates are converted more by their gut microbiota into short-chain fatty acids.[89]

Some glucose is converted to lactic acid by astrocytes, which is then utilized as an energy source by brain cells; some glucose is used by intestinal cells and red blood cells, while the rest reaches the liver, adipose tissue and muscle cells, where it is absorbed and stored as glycogen (under the influence of insulin). Liver cell glycogen can be converted to glucose and returned to the blood when insulin is low or absent; muscle cell glycogen is not returned to the blood because of a lack of enzymes. In fat cells, glucose is used to power reactions that synthesize some fat types and have other purposes. Glycogen is the body's "glucose energy storage" mechanism, because it is much more "space efficient" and less reactive than glucose itself.

As a result of its importance in human health, glucose is an analyte in glucose tests that are common medical blood tests.[90] Eating or fasting prior to taking a blood sample has an effect on analyses for glucose in the blood; a high fasting glucose blood sugar level may be a sign of prediabetes or diabetes mellitus.[91]

The glycemic index is an indicator of the speed of resorption and conversion to blood glucose levels from ingested carbohydrates, measured as the area under the curve of blood glucose levels after consumption in comparison to glucose (glucose is defined as 100).[92] The clinical importance of the glycemic index is controversial,[92][93] as foods with high fat contents slow the resorption of carbohydrates and lower the glycemic index, e.g. ice cream.[93] An alternative indicator is the insulin index,[94] measured as the impact of carbohydrate consumption on the blood insulin levels. The glycemic load is an indicator for the amount of glucose added to blood glucose levels after consumption, based on the glycemic index and the amount of consumed food.

Precursor Edit

Organisms use glucose as a precursor for the synthesis of several important substances. Starch, cellulose, and glycogen ("animal starch") are common glucose polymers (polysaccharides). Some of these polymers (starch or glycogen) serve as energy stores, while others (cellulose and chitin, which is made from a derivative of glucose) have structural roles. Oligosaccharides of glucose combined with other sugars serve as important energy stores. These include lactose, the predominant sugar in milk, which is a glucose-galactose disaccharide, and sucrose, another disaccharide which is composed of glucose and fructose. Glucose is also added onto certain proteins and lipids in a process called glycosylation. This is often critical for their functioning. The enzymes that join glucose to other molecules usually use phosphorylated glucose to power the formation of the new bond by coupling it with the breaking of the glucose-phosphate bond.

Other than its direct use as a monomer, glucose can be broken down to synthesize a wide variety of other biomolecules. This is important, as glucose serves both as a primary store of energy and as a source of organic carbon. Glucose can be broken down and converted into lipids. It is also a precursor for the synthesis of other important molecules such as vitamin C (ascorbic acid). In living organisms, glucose is converted to several other chemical compounds that are the starting material for various metabolic pathways. Among them, all other monosaccharides[95] such as fructose (via the polyol pathway),[49] mannose (the epimer of glucose at position 2), galactose (the epimer at position 4), fucose, various uronic acids and the amino sugars are produced from glucose.[51] In addition to the phosphorylation to glucose-6-phosphate, which is part of the glycolysis, glucose can be oxidized during its degradation to glucono-1,5-lactone. Glucose is used in some bacteria as a building block in the trehalose or the dextran biosynthesis and in animals as a building block of glycogen. Glucose can also be converted from bacterial xylose isomerase to fructose. In addition, glucose metabolites produce all nonessential amino acids, sugar alcohols such as mannitol and sorbitol, fatty acids, cholesterol and nucleic acids.[95] Finally, glucose is used as a building block in the glycosylation of proteins to glycoproteins, glycolipids, peptidoglycans, glycosides and other substances (catalyzed by glycosyltransferases) and can be cleaved from them by glycosidases.

Pathology Edit

Diabetes Edit

Diabetes is a metabolic disorder where the body is unable to regulate levels of glucose in the blood either because of a lack of insulin in the body or the failure, by cells in the body, to respond properly to insulin. Each of these situations can be caused by persistently high elevations of blood glucose levels, through pancreatic burnout and insulin resistance. The pancreas is the organ responsible for the secretion of the hormones insulin and glucagon.[96] Insulin is a hormone that regulates glucose levels, allowing the body's cells to absorb and use glucose. Without it, glucose cannot enter the cell and therefore cannot be used as fuel for the body's functions.[97] If the pancreas is exposed to persistently high elevations of blood glucose levels, the insulin-producing cells in the pancreas could be damaged, causing a lack of insulin in the body. Insulin resistance occurs when the pancreas tries to produce more and more insulin in response to persistently elevated blood glucose levels. Eventually, the rest of the body becomes resistant to the insulin that the pancreas is producing, thereby requiring more insulin to achieve the same blood glucose-lowering effect, and forcing the pancreas to produce even more insulin to compete with the resistance. This negative spiral contributes to pancreatic burnout, and the disease progression of diabetes.

To monitor the body's response to blood glucose-lowering therapy, glucose levels can be measured. Blood glucose monitoring can be performed by multiple methods, such as the fasting glucose test which measures the level of glucose in the blood after 8 hours of fasting. Another test is the 2-hour glucose tolerance test (GTT) – for this test, the person has a fasting glucose test done, then drinks a 75-gram glucose drink and is retested. This test measures the ability of the person's body to process glucose. Over time the blood glucose levels should decrease as insulin allows it to be taken up by cells and exit the blood stream.

Hypoglycemia management Edit

 
Glucose, 5% solution for infusions

Individuals with diabetes or other conditions that result in low blood sugar often carry small amounts of sugar in various forms. One sugar commonly used is glucose, often in the form of glucose tablets (glucose pressed into a tablet shape sometimes with one or more other ingredients as a binder), hard candy, or sugar packet.

Sources Edit

 
Glucose tablets

Most dietary carbohydrates contain glucose, either as their only building block (as in the polysaccharides starch and glycogen), or together with another monosaccharide (as in the hetero-polysaccharides sucrose and lactose).[98] Unbound glucose is one of the main ingredients of honey. Glucose is extremely abundant and has been isolated from a variety of natural sources across the world, including male cones of the coniferous tree Wollemia nobilis in Rome,[99] the roots of Ilex asprella plants in China,[100] and straws from rice in California.[101]

Sugar content of selected common plant foods (in grams per 100 g)[102]
Food
item 		Carbohydrate,
total,[a] including
dietary fiber 		Total
sugars 		Free
fructose 		Free
glucose 		Sucrose Ratio of
fructose/
glucose 		Sucrose as
proportion of
total sugars (%)
Fruits
Apple 13.8 10.4 5.9 2.4 2.1 2.0 19.9
Apricot 11.1 9.2 0.9 2.4 5.9 0.7 63.5
Banana 22.8 12.2 4.9 5.0 2.4 1.0 20.0
Fig, dried 63.9 47.9 22.9 24.8 0.9 0.93 0.15
Grapes 18.1 15.5 8.1 7.2 0.2 1.1 1
Navel orange 12.5 8.5 2.25 2.0 4.3 1.1 50.4
Peach 9.5 8.4 1.5 2.0 4.8 0.9 56.7
Pear 15.5 9.8 6.2 2.8 0.8 2.1 8.0
Pineapple 13.1 9.9 2.1 1.7 6.0 1.1 60.8
Plum 11.4 9.9 3.1 5.1 1.6 0.66 16.2
Vegetables
Beet, red 9.6 6.8 0.1 0.1 6.5 1.0 96.2
Carrot 9.6 4.7 0.6 0.6 3.6 1.0 77
Red pepper, sweet 6.0 4.2 2.3 1.9 0.0 1.2 0.0
Onion, sweet 7.6 5.0 2.0 2.3 0.7 0.9 14.3
Sweet potato 20.1 4.2 0.7 1.0 2.5 0.9 60.3
Yam 27.9 0.5 Traces Traces Traces — Traces
Sugar cane 13–18 0.2–1.0 0.2–1.0 11–16 1.0 high
Sugar beet 17–18 0.1–0.5 0.1–0.5 16–17 1.0 high
Grains
Corn, sweet 19.0 6.2 1.9 3.4 0.9 0.61 15.0
  1. ^ The carbohydrate value is calculated in the USDA database and does not always correspond to the sum of the sugars, the starch, and the "dietary fiber".

Commercial production Edit

Glucose is produced industrially from starch by enzymatic hydrolysis using glucose amylase or by the use of acids. Enzymatic hydrolysis has largely displaced acid-catalyzed hydrolysis reactions.[103] The result is glucose syrup (enzymatically with more than 90% glucose in the dry matter)[103] with an annual worldwide production volume of 20 million tonnes (as of 2011).[104] This is the reason for the former common name "starch sugar". The amylases most often come from Bacillus licheniformis[105] or Bacillus subtilis (strain MN-385),[105] which are more thermostable than the originally used enzymes.[105][106] Starting in 1982, pullulanases from Aspergillus niger were used in the production of glucose syrup to convert amylopectin to starch (amylose), thereby increasing the yield of glucose.[107] The reaction is carried out at a pH = 4.6–5.2 and a temperature of 55–60 °C.[9] Corn syrup has between 20% and 95% glucose in the dry matter.[108][109] The Japanese form of the glucose syrup, Mizuame, is made from sweet potato or rice starch.[110] Maltodextrin contains about 20% glucose.

Many crops can be used as the source of starch. Maize,[103] rice,[103] wheat,[103] cassava,[103] potato,[103] barley,[103] sweet potato,[111] corn husk and sago are all used in various parts of the world. In the United States, corn starch (from maize) is used almost exclusively. Some commercial glucose occurs as a component of invert sugar, a roughly 1:1 mixture of glucose and fructose that is produced from sucrose. In principle, cellulose could be hydrolyzed to glucose, but this process is not yet commercially practical.[26]

Conversion to fructose Edit

Main article: isoglucose

In the US, almost exclusively corn (more precisely, corn syrup) is used as glucose source for the production of isoglucose, which is a mixture of glucose and fructose, since fructose has a higher sweetening power – with same physiological calorific value of 374 kilocalories per 100 g. The annual world production of isoglucose is 8 million tonnes (as of 2011).[104] When made from corn syrup, the final product is high-fructose corn syrup (HFCS).

Commercial usage Edit

 
Relative sweetness of various sugars in comparison with sucrose[112]

Glucose is mainly used for the production of fructose and of glucose-containing foods. In foods, it is used as a sweetener, humectant, to increase the volume and to create a softer mouthfeel.[103] Various sources of glucose, such as grape juice (for wine) or malt (for beer), are used for fermentation to ethanol during the production of alcoholic beverages. Most soft drinks in the US use HFCS-55 (with a fructose content of 55% in the dry mass), while most other HFCS-sweetened foods in the US use HFCS-42 (with a fructose content of 42% in the dry mass).[113] In Mexico, on the other hand, soft drinks are sweetened by cane sugar, which has a higher sweetening power.[114] In addition, glucose syrup is used, inter alia, in the production of confectionery such as candies, toffee and fondant.[115] Typical chemical reactions of glucose when heated under water-free conditions are caramelization and, in presence of amino acids, the Maillard reaction.

In addition, various organic acids can be biotechnologically produced from glucose, for example by fermentation with Clostridium thermoaceticum to produce acetic acid, with Penicillium notatum for the production of araboascorbic acid, with Rhizopus delemar for the production of fumaric acid, with Aspergillus niger for the production of gluconic acid, with Candida brumptii to produce isocitric acid, with Aspergillus terreus for the production of itaconic acid, with Pseudomonas fluorescens for the production of 2-ketogluconic acid, with Gluconobacter suboxydans for the production of 5-ketogluconic acid, with Aspergillus oryzae for the production of kojic acid, with Lactobacillus delbrueckii for the production of lactic acid, with Lactobacillus brevis for the production of malic acid, with Propionibacter shermanii for the production of propionic acid, with Pseudomonas aeruginosa for the production of pyruvic acid and with Gluconobacter suboxydans for the production of tartaric acid.[116][additional citation(s) needed] Potent, bioactive natural products like triptolide that inhibit mammalian transcription via inhibition of the XPB subunit of the general transcription factor TFIIH has been recently reported as a glucose conjugate for targeting hypoxic cancer cells with increased glucose transporter expression.[117] Recently, glucose has been gaining commercial use as a key component of "kits" containing lactic acid and insulin intended to induce hypoglycemia and hyperlactatemia to combat different cancers and infections.[118]

Analysis Edit

When a glucose molecule is to be detected at a certain position in a larger molecule, nuclear magnetic resonance spectroscopy, X-ray crystallography analysis or lectin immunostaining is performed with concanavalin A reporter enzyme conjugate, which binds only glucose or mannose.

Classical qualitative detection reactions Edit

These reactions have only historical significance:

Fehling test Edit

The Fehling test is a classic method for the detection of aldoses.[119] Due to mutarotation, glucose is always present to a small extent as an open-chain aldehyde. By adding the Fehling reagents (Fehling (I) solution and Fehling (II) solution), the aldehyde group is oxidized to a carboxylic acid, while the Cu2+ tartrate complex is reduced to Cu+ and forms a brick red precipitate (Cu2O).

Tollens test Edit

In the Tollens test, after addition of ammoniacal AgNO3 to the sample solution, glucose reduces Ag+ to elemental silver.[120]

Barfoed test Edit

In Barfoed's test,[121] a solution of dissolved copper acetate, sodium acetate and acetic acid is added to the solution of the sugar to be tested and subsequently heated in a water bath for a few minutes. Glucose and other monosaccharides rapidly produce a reddish color and reddish brown copper(I) oxide (Cu2O).

Nylander's test Edit

As a reducing sugar, glucose reacts in the Nylander's test.[122]

Other tests Edit

See also: Maillard reaction and Lye roll

Upon heating a dilute potassium hydroxide solution with glucose to 100 °C, a strong reddish browning and a caramel-like odor develops.[123] Concentrated sulfuric acid dissolves dry glucose without blackening at room temperature forming sugar sulfuric acid.[123][verification needed] In a yeast solution, alcoholic fermentation produces carbon dioxide in the ratio of 2.0454 molecules of glucose to one molecule of CO2.[123] Glucose forms a black mass with stannous chloride.[123] In an ammoniacal silver solution, glucose (as well as lactose and dextrin) leads to the deposition of silver. In an ammoniacal lead acetate solution, white lead glycoside is formed in the presence of glucose, which becomes less soluble on cooking and turns brown.[123] In an ammoniacal copper solution, yellow copper oxide hydrate is formed with glucose at room temperature, while red copper oxide is formed during boiling (same with dextrin, except for with an ammoniacal copper acetate solution).[123] With Hager's reagent, glucose forms mercury oxide during boiling.[123] An alkaline bismuth solution is used to precipitate elemental, black-brown bismuth with glucose.[123] Glucose boiled in an ammonium molybdate solution turns the solution blue. A solution with indigo carmine and sodium carbonate destains when boiled with glucose.[123]

Instrumental quantification Edit

Refractometry and polarimetry Edit

In concentrated solutions of glucose with a low proportion of other carbohydrates, its concentration can be determined with a polarimeter. For sugar mixtures, the concentration can be determined with a refractometer, for example in the Oechsle determination in the course of the production of wine.

Photometric enzymatic methods in solution Edit

Main article: Glucose oxidation reaction

The enzyme glucose oxidase (GOx) converts glucose into gluconic acid and hydrogen peroxide while consuming oxygen. Another enzyme, peroxidase, catalyzes a chromogenic reaction (Trinder reaction)[124] of phenol with 4-aminoantipyrine to a purple dye.

Photometric test-strip method Edit

The test-strip method employs the above-mentioned enzymatic conversion of glucose to gluconic acid to form hydrogen peroxide. The reagents are immobilised on a polymer matrix, the so-called test strip, which assumes a more or less intense color. This can be measured reflectometrically at 510 nm with the aid of an LED-based handheld photometer. This allows routine blood sugar determination by nonscientists. In addition to the reaction of phenol with 4-aminoantipyrine, new chromogenic reactions have been developed that allow photometry at higher wavelengths (550 nm, 750 nm).[125]

Amperometric glucose sensor Edit

The electroanalysis of glucose is also based on the enzymatic reaction mentioned above. The produced hydrogen peroxide can be amperometrically quantified by anodic oxidation at a potential of 600 mV.[126] The GOx is immobilized on the electrode surface or in a membrane placed close to the electrode. Precious metals such as platinum or gold are used in electrodes, as well as carbon nanotube electrodes, which e.g. are doped with boron.[127] Cu–CuO nanowires are also used as enzyme-free amperometric electrodes, reaching a detection limit of 50 μmol/L.[128] A particularly promising method is the so-called "enzyme wiring", where the electron flowing during the oxidation is transferred via a molecular wire directly from the enzyme to the electrode.[129]

Other sensory methods Edit

There are a variety of other chemical sensors for measuring glucose.[130][131] Given the importance of glucose analysis in the life sciences, numerous optical probes have also been developed for saccharides based on the use of boronic acids,[132] which are particularly useful for intracellular sensory applications where other (optical) methods are not or only conditionally usable. In addition to the organic boronic acid derivatives, which often bind highly specifically to the 1,2-diol groups of sugars, there are also other probe concepts classified by functional mechanisms which use selective glucose-binding proteins (e.g. concanavalin A) as a receptor. Furthermore, methods were developed which indirectly detect the glucose concentration via the concentration of metabolized products, e.g. by the consumption of oxygen using fluorescence-optical sensors.[133] Finally, there are enzyme-based concepts that use the intrinsic absorbance or fluorescence of (fluorescence-labeled) enzymes as reporters.[130]

Copper iodometry Edit

Glucose can be quantified by copper iodometry.[134]

Chromatographic methods Edit

In particular, for the analysis of complex mixtures containing glucose, e.g. in honey, chromatographic methods such as high performance liquid chromatography and gas chromatography[134] are often used in combination with mass spectrometry.[135][136] Taking into account the isotope ratios, it is also possible to reliably detect honey adulteration by added sugars with these methods.[137] Derivatization using silylation reagents is commonly used.[138] Also, the proportions of di- and trisaccharides can be quantified.

In vivo analysis Edit

Glucose uptake in cells of organisms is measured with 2-deoxy-D-glucose or fluorodeoxyglucose.[83] (18F)fluorodeoxyglucose is used as a tracer in positron emission tomography in oncology and neurology,[139] where it is by far the most commonly used diagnostic agent.[140]

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Wikimedia Commons has media related to Glucose.

August 26, 2023
glucose, sugar, with, molecular, formula, c6h12o6, overall, most, abundant, monosaccharide, subcategory, carbohydrates, mainly, made, plants, most, algae, during, photosynthesis, from, water, carbon, dioxide, using, energy, from, sunlight, where, used, make, c. Glucose is a sugar with the molecular formula C6H12O6 Glucose is overall the most abundant monosaccharide 3 a subcategory of carbohydrates Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide using energy from sunlight where it is used to make cellulose in cell walls the most abundant carbohydrate in the world 4 d Glucose Skeletal formula of d glucoseHaworth projection of a d glucopyranoseFischer projection of d glucoseNamesPronunciation ˈ ɡ l uː k oʊ z ɡ l uː k oʊ s IUPAC name Systematic name 2R 3S 4R 5R 2 3 4 5 6 PentahydroxyhexanalAllowed trivial names ᴅ Glucoseᴅ gluco HexosePreferred IUPAC name PINs are not identified for natural products Systematic IUPAC name 3R 4S 5S 6R 6 hydroxymethyl oxane 2 3 4 5 tetrol cyclic Other names Blood sugarsDextroseCorn sugard GlucoseGrape sugarIdentifiersCAS Number 50 99 7 Y492 62 6 a d glucopyranose Y3D model JSmol Interactive imageInteractive image3DMet B01203Abbreviations GlcBeilstein Reference 1281604ChEBI CHEBI 4167 YChEMBL ChEMBL1222250 YChemSpider 5589 YEC Number 200 075 1Gmelin Reference 83256IUPHAR BPS 4536KEGG C00031 YMeSH GlucosePubChem CID 5793RTECS number LZ6600000UNII 5SL0G7R0OK Y5J5I9EB41E a d glucopyranose YInChI InChI 1S C6H12O6 c7 1 2 3 8 4 9 5 10 6 11 12 2 h2 11H 1H2 t2 3 4 5 6 m1 s1 YKey WQZGKKKJIJFFOK GASJEMHNSA N YSMILES OC C H 1OC O C H O C H O C H 1OC C H 1 C H C H C H C H O1 O O O O OPropertiesChemical formula C 6H 12O 6Molar mass 180 156 g molAppearance White powderDensity 1 54 g cm3Melting point a d Glucose 146 C 295 F 419 K b d Glucose 150 C 302 F 423 K Solubility in water 909 g L 25 C 77 F Magnetic susceptibility x 101 5 10 6 cm3 molDipole moment 8 6827ThermochemistryHeat capacity C 218 6 J K mol 1 Std molarentropy S 298 209 2 J K mol 1 Std enthalpy offormation DfH 298 1271 kJ mol 2 Heat of combustion higher value HHV 2 805 kJ mol 670 kcal mol PharmacologyATC code B05CX01 WHO V04CA02 WHO V06DC01 WHO HazardsNFPA 704 fire diamond 010Safety data sheet SDS ICSC 08655Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references In energy metabolism glucose is the most important source of energy in all organisms Glucose for metabolism is stored as a polymer in plants mainly as starch and amylopectin and in animals as glycogen Glucose circulates in the blood of animals as blood sugar The naturally occurring form of glucose is d glucose while its stereoisomer l glucose is produced synthetically in comparatively small amounts and is less biologically active 5 Glucose is a monosaccharide containing six carbon atoms and an aldehyde group and is therefore an aldohexose The glucose molecule can exist in an open chain acyclic as well as ring cyclic form Glucose is naturally occurring and is found in its free state in fruits and other parts of plants In animals glucose is released from the breakdown of glycogen in a process known as glycogenolysis Glucose as intravenous sugar solution is on the World Health Organization s List of Essential Medicines 6 It is also on the list in combination with sodium chloride 6 The name glucose is derived from Ancient Greek gleῦkos gleukos wine must from glykys glykys sweet 7 8 The suffix ose is a chemical classifier denoting a sugar Contents 1 History 2 Chemical and physical properties 2 1 Structure and nomenclature 2 2 Open chain form 2 3 Cyclic forms 2 4 Mutarotation 2 5 Optical activity 2 6 Isomerisation 3 Biochemical properties 3 1 Uptake 3 2 Biosynthesis 3 3 Glucose degradation 3 4 Energy source 3 5 Precursor 4 Pathology 4 1 Diabetes 4 2 Hypoglycemia management 5 Sources 6 Commercial production 6 1 Conversion to fructose 7 Commercial usage 8 Analysis 8 1 Classical qualitative detection reactions 8 1 1 Fehling test 8 1 2 Tollens test 8 1 3 Barfoed test 8 1 4 Nylander s test 8 1 5 Other tests 8 2 Instrumental quantification 8 2 1 Refractometry and polarimetry 8 2 2 Photometric enzymatic methods in solution 8 2 3 Photometric test strip method 8 2 4 Amperometric glucose sensor 8 2 5 Other sensory methods 8 2 6 Copper iodometry 8 3 Chromatographic methods 8 3 1 In vivo analysis 9 ReferencesHistory EditGlucose was first isolated from raisins in 1747 by the German chemist Andreas Marggraf 9 10 Glucose was discovered in grapes by another German chemist Johann Tobias Lowitz in 1792 and distinguished as being different from cane sugar sucrose Glucose is the term coined by Jean Baptiste Dumas in 1838 which has prevailed in the chemical literature Friedrich August Kekule proposed the term dextrose from the Latin dexter meaning right because in aqueous solution of glucose the plane of linearly polarized light is turned to the right In contrast l fructose a ketohexose and l glucose turn linearly polarized light to the left The earlier notation according to the rotation of the plane of linearly polarized light d and l nomenclature was later abandoned in favor of the d and l notation which refers to the absolute configuration of the asymmetric center farthest from the carbonyl group and in concordance with the configuration of d or l glyceraldehyde 11 12 Since glucose is a basic necessity of many organisms a correct understanding of its chemical makeup and structure contributed greatly to a general advancement in organic chemistry This understanding occurred largely as a result of the investigations of Emil Fischer a German chemist who received the 1902 Nobel Prize in Chemistry for his findings 13 The synthesis of glucose established the structure of organic material and consequently formed the first definitive validation of Jacobus Henricus van t Hoff s theories of chemical kinetics and the arrangements of chemical bonds in carbon bearing molecules 14 Between 1891 and 1894 Fischer established the stereochemical configuration of all the known sugars and correctly predicted the possible isomers applying Van t Hoff s theory of asymmetrical carbon atoms The names initially referred to the natural substances Their enantiomers were given the same name with the introduction of systematic nomenclatures taking into account absolute stereochemistry e g Fischer nomenclature d l nomenclature For the discovery of the metabolism of glucose Otto Meyerhof received the Nobel Prize in Physiology or Medicine in 1922 15 Hans von Euler Chelpin was awarded the Nobel Prize in Chemistry along with Arthur Harden in 1929 for their research on the fermentation of sugar and their share of enzymes in this process 16 17 In 1947 Bernardo Houssay for his discovery of the role of the pituitary gland in the metabolism of glucose and the derived carbohydrates as well as Carl and Gerty Cori for their discovery of the conversion of glycogen from glucose received the Nobel Prize in Physiology or Medicine 18 19 20 In 1970 Luis Leloir was awarded the Nobel Prize in Chemistry for the discovery of glucose derived sugar nucleotides in the biosynthesis of carbohydrates 21 Chemical and physical properties EditGlucose forms white or colorless solids that are highly soluble in water and acetic acid but poorly soluble in methanol and ethanol They melt at 146 C 295 F a and 150 C 302 F b and decompose starting at 188 C 370 F with release of various volatile products ultimately leaving a residue of carbon 22 Glucose has a pK value of 12 16 at 25 C 77 F in water 23 With six carbon atoms it is classed as a hexose a subcategory of the monosaccharides d Glucose is one of the sixteen aldohexose stereoisomers The d isomer d glucose also known as dextrose occurs widely in nature but the l isomer l glucose does not Glucose can be obtained by hydrolysis of carbohydrates such as milk sugar lactose cane sugar sucrose maltose cellulose glycogen etc Dextrose is commonly commercially manufactured from cornstarch in the US and Japan from potato and wheat starch in Europe and from tapioca starch in tropical areas 24 The manufacturing process uses hydrolysis via pressurized steaming at controlled pH in a jet followed by further enzymatic depolymerization 25 Unbonded glucose is one of the main ingredients of honey Structure and nomenclature Edit See also Mutarotation Mutarotation of glucoseGlucose is usually present in solid form as a monohydrate with a closed pyran ring dextrose hydrate In aqueous solution on the other hand it is an open chain to a small extent and is present predominantly as a or b pyranose which interconvert From aqueous solutions the three known forms can be crystallized a glucopyranose b glucopyranose and b glucopyranose hydrate 26 Glucose is a building block of the disaccharides lactose and sucrose cane or beet sugar of oligosaccharides such as raffinose and of polysaccharides such as starch amylopectin glycogen and cellulose The glass transition temperature of glucose is 31 C 88 F and the Gordon Taylor constant an experimentally determined constant for the prediction of the glass transition temperature for different mass fractions of a mixture of two substances 27 is 4 5 28 Forms and projections of d glucose in comparisonNatta projection Haworth projection a d glucofuranose b d glucofuranose a d glucopyranose b d glucopyranosea d Glucopyranose in 1 Tollens Fischer 2 Haworth projection 3 chair conformation 4 Mills projection Open chain form Edit Glucose can exist in both a straight chain and ring form The open chain form of glucose makes up less than 0 02 of the glucose molecules in an aqueous solution at equilibrium 29 The rest is one of two cyclic hemiacetal forms In its open chain form the glucose molecule has an open as opposed to cyclic unbranched backbone of six carbon atoms where C 1 is part of an aldehyde group H C O Therefore glucose is also classified as an aldose or an aldohexose The aldehyde group makes glucose a reducing sugar giving a positive reaction with the Fehling test Cyclic forms Edit Cyclic forms of glucose From left to right Haworth projections and ball and stick structures of the a and b anomers of D glucopyranose top row and D glucofuranose bottom row In solutions the open chain form of glucose either D or L exists in equilibrium with several cyclic isomers each containing a ring of carbons closed by one oxygen atom In aqueous solution however more than 99 of glucose molecules exist as pyranose forms The open chain form is limited to about 0 25 and furanose forms exist in negligible amounts The terms glucose and D glucose are generally used for these cyclic forms as well The ring arises from the open chain form by an intramolecular nucleophilic addition reaction between the aldehyde group at C 1 and either the C 4 or C 5 hydroxyl group forming a hemiacetal linkage C OH H O The reaction between C 1 and C 5 yields a six membered heterocyclic system called a pyranose which is a monosaccharide sugar hence ose containing a derivatised pyran skeleton The much rarer reaction between C 1 and C 4 yields a five membered furanose ring named after the cyclic ether furan In either case each carbon in the ring has one hydrogen and one hydroxyl attached except for the last carbon C 4 or C 5 where the hydroxyl is replaced by the remainder of the open molecule which is C CH2OH HOH H or CHOH H respectively The ring closing reaction can give two products denoted a and b When a glucopyranose molecule is drawn in the Haworth projection the designation a means that the hydroxyl group attached to C 1 and the CH2OH group at C 5 lies on opposite sides of the ring s plane atrans arrangement while b means that they are on the same side of the plane acis arrangement Therefore the open chain isomer D glucose gives rise to four distinct cyclic isomers a D glucopyranose b D glucopyranose a D glucofuranose and b D glucofuranose These five structures exist in equilibrium and interconvert and the interconversion is much more rapid with acid catalysis Widely proposed arrow pushing mechanism for acid catalyzed dynamic equilibrium between the a and b anomers of D glucopyranose Chair conformations of a left and b right D glucopyranose The other open chain isomer L glucose similarly gives rise to four distinct cyclic forms of L glucose each the mirror image of the corresponding D glucose The glucopyranose ring a or b can assume several non planar shapes analogous to the chair and boat conformations of cyclohexane Similarly the glucofuranose ring may assume several shapes analogous to the envelope conformations of cyclopentane In the solid state only the glucopyranose forms are observed Some derivatives of glucofuranose such as 1 2 O isopropylidene D glucofuranose are stable and can be obtained pure as crystalline solids 30 31 For example reaction of a D glucose with para tolylboronic acid H3C C6H4 B OH 2 reforms the normal pyranose ring to yield the 4 fold ester a D glucofuranose 1 2 3 5 bis p tolylboronate 32 Mutarotation Edit Mutarotation d glucose molecules exist as cyclic hemiacetals that are epimeric diastereomeric to each other The epimeric ratio a b is 36 64 In the a D glucopyranose left the blue labelled hydroxy group is in the axial position at the anomeric centre whereas in the b D glucopyranose right the blue labelled hydroxy group is in equatorial position at the anomeric centre Mutarotation consists of a temporary reversal of the ring forming reaction resulting in the open chain form followed by a reforming of the ring The ring closure step may use a different OH group than the one recreated by the opening step thus switching between pyranose and furanose forms or the new hemiacetal group created on C 1 may have the same or opposite handedness as the original one thus switching between the a and b forms Thus though the open chain form is barely detectable in solution it is an essential component of the equilibrium The open chain form is thermodynamically unstable and it spontaneously isomerizes to the cyclic forms Although the ring closure reaction could in theory create four or three atom rings these would be highly strained and are not observed in practice In solutions at room temperature the four cyclic isomers interconvert over a time scale of hours in a process called mutarotation 33 Starting from any proportions the mixture converges to a stable ratio of a b 36 64 The ratio would be a b 11 89 if it were not for the influence of the anomeric effect 34 Mutarotation is considerably slower at temperatures close to 0 C 32 F Optical activity Edit Whether in water or the solid form d glucose is dextrorotatory meaning it will rotate the direction of polarized light clockwise as seen looking toward the light source The effect is due to the chirality of the molecules and indeed the mirror image isomer l glucose is levorotatory rotates polarized light counterclockwise by the same amount The strength of the effect is different for each of the five tautomers Note that the d prefix does not refer directly to the optical properties of the compound It indicates that the C 5 chiral centre has the same handedness as that of d glyceraldehyde which was so labelled because it is dextrorotatory The fact that d glucose is dextrorotatory is a combined effect of its four chiral centres not just of C 5 and indeed some of the other d aldohexoses are levorotatory The conversion between the two anomers can be observed in a polarimeter since pure a d glucose has a specific rotation angle of 112 2 mL dm g pure b d glucose of 17 5 mL dm g 35 When equilibrium has been reached after a certain time due to mutarotation the angle of rotation is 52 7 mL dm g 35 By adding acid or base this transformation is much accelerated The equilibration takes place via the open chain aldehyde form Isomerisation Edit In dilute sodium hydroxide or other dilute bases the monosaccharides mannose glucose and fructose interconvert via a Lobry de Bruyn Alberda Van Ekenstein transformation so that a balance between these isomers is formed This reaction proceeds via an enediol Biochemical properties EditMetabolism of common monosaccharides and some biochemical reactions of glucose Glucose is the most abundant monosaccharide Glucose is also the most widely used aldohexose in most living organisms One possible explanation for this is that glucose has a lower tendency than other aldohexoses to react nonspecifically with the amine groups of proteins 36 This reaction glycation impairs or destroys the function of many proteins 36 e g in glycated hemoglobin Glucose s low rate of glycation can be attributed to its having a more stable cyclic form compared to other aldohexoses which means it spends less time than they do in its reactive open chain form 36 The reason for glucose having the most stable cyclic form of all the aldohexoses is that its hydroxy groups with the exception of the hydroxy group on the anomeric carbon of d glucose are in the equatorial position Presumably glucose is the most abundant natural monosaccharide because it is less glycated with proteins than other monosaccharides 36 37 Another hypothesis is that glucose being the only d aldohexose that has all five hydroxy substituents in the equatorial position in the form of b d glucose is more readily accessible to chemical reactions 38 194 199 for example for esterification 39 363 or acetal formation 40 For this reason d glucose is also a highly preferred building block in natural polysaccharides glycans Polysaccharides that are composed solely of glucose are termed glucans Glucose is produced by plants through photosynthesis using sunlight water and carbon dioxide and can be used by all living organisms as an energy and carbon source However most glucose does not occur in its free form but in the form of its polymers i e lactose sucrose starch and others which are energy reserve substances and cellulose and chitin which are components of the cell wall in plants or fungi and arthropods respectively These polymers when consumed by animals fungi and bacteria are degraded to glucose using enzymes All animals are also able to produce glucose themselves from certain precursors as the need arises Neurons cells of the renal medulla and erythrocytes depend on glucose for their energy production 41 In adult humans there is about 18 g 0 63 oz of glucose 42 of which about 4 g 0 14 oz is present in the blood 43 Approximately 180 220 g 6 3 7 8 oz of glucose is produced in the liver of an adult in 24 hours 42 Many of the long term complications of diabetes e g blindness kidney failure and peripheral neuropathy are probably due to the glycation of proteins or lipids 44 In contrast enzyme regulated addition of sugars to protein is called glycosylation and is essential for the function of many proteins 45 Uptake Edit Ingested glucose initially binds to the receptor for sweet taste on the tongue in humans This complex of the proteins T1R2 and T1R3 makes it possible to identify glucose containing food sources Glucose mainly comes from food about 300 g 11 oz per day is produced by conversion of food 46 but it is also synthesized from other metabolites in the body s cells In humans the breakdown of glucose containing polysaccharides happens in part already during chewing by means of amylase which is contained in saliva as well as by maltase lactase and sucrase on the brush border of the small intestine Glucose is a building block of many carbohydrates and can be split off from them using certain enzymes Glucosidases a subgroup of the glycosidases first catalyze the hydrolysis of long chain glucose containing polysaccharides removing terminal glucose In turn disaccharides are mostly degraded by specific glycosidases to glucose The names of the degrading enzymes are often derived from the particular poly and disaccharide inter alia for the degradation of polysaccharide chains there are amylases named after amylose a component of starch cellulases named after cellulose chitinases named after chitin and more Furthermore for the cleavage of disaccharides there are maltase lactase sucrase trehalase and others In humans about 70 genes are known that code for glycosidases They have functions in the digestion and degradation of glycogen sphingolipids mucopolysaccharides and poly ADP ribose Humans do not produce cellulases chitinases or trehalases but the bacteria in the gut microbiota do In order to get into or out of cell membranes of cells and membranes of cell compartments glucose requires special transport proteins from the major facilitator superfamily In the small intestine more precisely in the jejunum 47 glucose is taken up into the intestinal epithelium with the help of glucose transporters 48 via a secondary active transport mechanism called sodium ion glucose symport via sodium glucose cotransporter 1 SGLT1 49 Further transfer occurs on the basolateral side of the intestinal epithelial cells via the glucose transporter GLUT2 49 as well uptake into liver cells kidney cells cells of the islets of Langerhans neurons astrocytes and tanycytes 50 Glucose enters the liver via the portal vein and is stored there as a cellular glycogen 51 In the liver cell it is phosphorylated by glucokinase at position 6 to form glucose 6 phosphate which cannot leave the cell Glucose 6 phosphatase can convert glucose 6 phosphate back into glucose exclusively in the liver so the body can maintain a sufficient blood glucose concentration In other cells uptake happens by passive transport through one of the 14 GLUT proteins 49 In the other cell types phosphorylation occurs through a hexokinase whereupon glucose can no longer diffuse out of the cell The glucose transporter GLUT1 is produced by most cell types and is of particular importance for nerve cells and pancreatic b cells 49 GLUT3 is highly expressed in nerve cells 49 Glucose from the bloodstream is taken up by GLUT4 from muscle cells of the skeletal muscle 52 and heart muscle and fat cells 53 GLUT14 is expressed exclusively in testicles 54 Excess glucose is broken down and converted into fatty acids which are stored as triglycerides In the kidneys glucose in the urine is absorbed via SGLT1 and SGLT2 in the apical cell membranes and transmitted via GLUT2 in the basolateral cell membranes 55 About 90 of kidney glucose reabsorption is via SGLT2 and about 3 via SGLT1 56 Biosynthesis Edit Main articles Gluconeogenesis and Glycogenolysis In plants and some prokaryotes glucose is a product of photosynthesis 57 Glucose is also formed by the breakdown of polymeric forms of glucose like glycogen in animals and mushrooms or starch in plants The cleavage of glycogen is termed glycogenolysis the cleavage of starch is called starch degradation 58 The metabolic pathway that begins with molecules containing two to four carbon atoms C and ends in the glucose molecule containing six carbon atoms is called gluconeogenesis and occurs in all living organisms The smaller starting materials are the result of other metabolic pathways Ultimately almost all biomolecules come from the assimilation of carbon dioxide in plants and microbes during photosynthesis 39 359 The free energy of formation of a d glucose is 917 2 kilojoules per mole 39 59 In humans gluconeogenesis occurs in the liver and kidney 59 but also in other cell types In the liver about 150 g 5 3 oz of glycogen are stored in skeletal muscle about 250 g 8 8 oz 60 However the glucose released in muscle cells upon cleavage of the glycogen can not be delivered to the circulation because glucose is phosphorylated by the hexokinase and a glucose 6 phosphatase is not expressed to remove the phosphate group Unlike for glucose there is no transport protein for glucose 6 phosphate Gluconeogenesis allows the organism to build up glucose from other metabolites including lactate or certain amino acids while consuming energy The renal tubular cells can also produce glucose Glucose also can be found outside of living organisms in the ambient environment Glucose concentrations in the atmosphere are detected via collection of samples by aircraft and are known to vary from location to location For example glucose concentrations in atmospheric air from inland China range from 0 8 to 20 1 pg L whereas east coastal China glucose concentrations range from 10 3 to 142 pg L 61 Glucose degradation Edit Glucose metabolism and various forms of it in the process Glucose containing compounds and isomeric forms are digested and taken up by the body in the intestines including starch glycogen disaccharides and monosaccharides Glucose is stored in mainly the liver and muscles as glycogen It is distributed and used in tissues as free glucose Main articles Glycolysis and Pentose phosphate pathway In humans glucose is metabolized by glycolysis 62 and the pentose phosphate pathway 63 Glycolysis is used by all living organisms 38 551 64 with small variations and all organisms generate energy from the breakdown of monosaccharides 64 In the further course of the metabolism it can be completely degraded via oxidative decarboxylation the citric acid cycle synonym Krebs cycle and the respiratory chain to water and carbon dioxide If there is not enough oxygen available for this the glucose degradation in animals occurs anaerobic to lactate via lactic acid fermentation and releases much less energy Muscular lactate enters the liver through the bloodstream in mammals where gluconeogenesis occurs Cori cycle With a high supply of glucose the metabolite acetyl CoA from the Krebs cycle can also be used for fatty acid synthesis 65 Glucose is also used to replenish the body s glycogen stores which are mainly found in liver and skeletal muscle These processes are hormonally regulated In other living organisms other forms of fermentation can occur The bacterium Escherichia coli can grow on nutrient media containing glucose as the sole carbon source 39 59 In some bacteria and in modified form also in archaea glucose is degraded via the Entner Doudoroff pathway 66 Use of glucose as an energy source in cells is by either aerobic respiration anaerobic respiration or fermentation The first step of glycolysis is the phosphorylation of glucose by a hexokinase to form glucose 6 phosphate The main reason for the immediate phosphorylation of glucose is to prevent its diffusion out of the cell as the charged phosphate group prevents glucose 6 phosphate from easily crossing the cell membrane 67 Furthermore addition of the high energy phosphate group activates glucose for subsequent breakdown in later steps of glycolysis At physiological conditions this initial reaction is irreversible In anaerobic respiration one glucose molecule produces a net gain of two ATP molecules four ATP molecules are produced during glycolysis through substrate level phosphorylation but two are required by enzymes used during the process 68 In aerobic respiration a molecule of glucose is much more profitable in that a maximum net production of 30 or 32 ATP molecules depending on the organism is generated 69 Click on genes proteins and metabolites below to link to respective articles 1 File alt Glycolysis and Gluconeogenesis edit Glycolysis and Gluconeogenesis edit The interactive pathway map can be edited at WikiPathways GlycolysisGluconeogenesis WP534 Tumor cells often grow comparatively quickly and consume an above average amount of glucose by glycolysis 70 which leads to the formation of lactate the end product of fermentation in mammals even in the presence of oxygen This is called the Warburg effect For the increased uptake of glucose in tumors various SGLT and GLUT are overly produced 71 72 In yeast ethanol is fermented at high glucose concentrations even in the presence of oxygen which normally leads to respiration rather than fermentation This is called the Crabtree effect Glucose can also degrade to form carbon dioxide through abiotic means This has been demonstrated to occur experimentally via oxidation and hydrolysis at 22 C and a pH of 2 5 73 Energy source Edit Diagram showing the possible intermediates in glucose degradation Metabolic pathways orange glycolysis green Entner Doudoroff pathway phosphorylating yellow Entner Doudoroff pathway non phosphorylatingGlucose is a ubiquitous fuel in biology It is used as an energy source in organisms from bacteria to humans through either aerobic respiration anaerobic respiration in bacteria or fermentation Glucose is the human body s key source of energy through aerobic respiration providing about 3 75 kilocalories 16 kilojoules of food energy per gram 74 Breakdown of carbohydrates e g starch yields mono and disaccharides most of which is glucose Through glycolysis and later in the reactions of the citric acid cycle and oxidative phosphorylation glucose is oxidized to eventually form carbon dioxide and water yielding energy mostly in the form of ATP The insulin reaction and other mechanisms regulate the concentration of glucose in the blood The physiological caloric value of glucose depending on the source is 16 2 kilojoules per gram 75 or 15 7 kJ g 3 74 kcal g 76 The high availability of carbohydrates from plant biomass has led to a variety of methods during evolution especially in microorganisms to utilize glucose for energy and carbon storage Differences exist in which end product can no longer be used for energy production The presence of individual genes and their gene products the enzymes determine which reactions are possible The metabolic pathway of glycolysis is used by almost all living beings An essential difference in the use of glycolysis is the recovery of NADPH as a reductant for anabolism that would otherwise have to be generated indirectly 77 Glucose and oxygen supply almost all the energy for the brain 78 so its availability influences psychological processes When glucose is low psychological processes requiring mental effort e g self control effortful decision making are impaired 79 80 81 82 In the brain which is dependent on glucose and oxygen as the major source of energy the glucose concentration is usually 4 to 6 mM 5 mM equals 90 mg dL 42 but decreases to 2 to 3 mM when fasting 83 Confusion occurs below 1 mM and coma at lower levels 83 The glucose in the blood is called blood sugar Blood sugar levels are regulated by glucose binding nerve cells in the hypothalamus 84 In addition glucose in the brain binds to glucose receptors of the reward system in the nucleus accumbens 84 The binding of glucose to the sweet receptor on the tongue induces a release of various hormones of energy metabolism either through glucose or through other sugars leading to an increased cellular uptake and lower blood sugar levels 85 Artificial sweeteners do not lower blood sugar levels 85 The blood sugar content of a healthy person in the short time fasting state e g after overnight fasting is about 70 to 100 mg dL of blood 4 to 5 5 mM In blood plasma the measured values are about 10 15 higher In addition the values in the arterial blood are higher than the concentrations in the venous blood since glucose is absorbed into the tissue during the passage of the capillary bed Also in the capillary blood which is often used for blood sugar determination the values are sometimes higher than in the venous blood The glucose content of the blood is regulated by the hormones insulin incretin and glucagon 84 86 Insulin lowers the glucose level glucagon increases it 42 Furthermore the hormones adrenaline thyroxine glucocorticoids somatotropin and adrenocorticotropin lead to an increase in the glucose level 42 There is also a hormone independent regulation which is referred to as glucose autoregulation 87 After food intake the blood sugar concentration increases Values over 180 mg dL in venous whole blood are pathological and are termed hyperglycemia values below 40 mg dL are termed hypoglycaemia 88 When needed glucose is released into the bloodstream by glucose 6 phosphatase from glucose 6 phosphate originating from liver and kidney glycogen thereby regulating the homeostasis of blood glucose concentration 59 41 In ruminants the blood glucose concentration is lower 60 mg dL in cattle and 40 mg dL in sheep because the carbohydrates are converted more by their gut microbiota into short chain fatty acids 89 Some glucose is converted to lactic acid by astrocytes which is then utilized as an energy source by brain cells some glucose is used by intestinal cells and red blood cells while the rest reaches the liver adipose tissue and muscle cells where it is absorbed and stored as glycogen under the influence of insulin Liver cell glycogen can be converted to glucose and returned to the blood when insulin is low or absent muscle cell glycogen is not returned to the blood because of a lack of enzymes In fat cells glucose is used to power reactions that synthesize some fat types and have other purposes Glycogen is the body s glucose energy storage mechanism because it is much more space efficient and less reactive than glucose itself As a result of its importance in human health glucose is an analyte in glucose tests that are common medical blood tests 90 Eating or fasting prior to taking a blood sample has an effect on analyses for glucose in the blood a high fasting glucose blood sugar level may be a sign of prediabetes or diabetes mellitus 91 The glycemic index is an indicator of the speed of resorption and conversion to blood glucose levels from ingested carbohydrates measured as the area under the curve of blood glucose levels after consumption in comparison to glucose glucose is defined as 100 92 The clinical importance of the glycemic index is controversial 92 93 as foods with high fat contents slow the resorption of carbohydrates and lower the glycemic index e g ice cream 93 An alternative indicator is the insulin index 94 measured as the impact of carbohydrate consumption on the blood insulin levels The glycemic load is an indicator for the amount of glucose added to blood glucose levels after consumption based on the glycemic index and the amount of consumed food Precursor Edit Organisms use glucose as a precursor for the synthesis of several important substances Starch cellulose and glycogen animal starch are common glucose polymers polysaccharides Some of these polymers starch or glycogen serve as energy stores while others cellulose and chitin which is made from a derivative of glucose have structural roles Oligosaccharides of glucose combined with other sugars serve as important energy stores These include lactose the predominant sugar in milk which is a glucose galactose disaccharide and sucrose another disaccharide which is composed of glucose and fructose Glucose is also added onto certain proteins and lipids in a process called glycosylation This is often critical for their functioning The enzymes that join glucose to other molecules usually use phosphorylated glucose to power the formation of the new bond by coupling it with the breaking of the glucose phosphate bond Other than its direct use as a monomer glucose can be broken down to synthesize a wide variety of other biomolecules This is important as glucose serves both as a primary store of energy and as a source of organic carbon Glucose can be broken down and converted into lipids It is also a precursor for the synthesis of other important molecules such as vitamin C ascorbic acid In living organisms glucose is converted to several other chemical compounds that are the starting material for various metabolic pathways Among them all other monosaccharides 95 such as fructose via the polyol pathway 49 mannose the epimer of glucose at position 2 galactose the epimer at position 4 fucose various uronic acids and the amino sugars are produced from glucose 51 In addition to the phosphorylation to glucose 6 phosphate which is part of the glycolysis glucose can be oxidized during its degradation to glucono 1 5 lactone Glucose is used in some bacteria as a building block in the trehalose or the dextran biosynthesis and in animals as a building block of glycogen Glucose can also be converted from bacterial xylose isomerase to fructose In addition glucose metabolites produce all nonessential amino acids sugar alcohols such as mannitol and sorbitol fatty acids cholesterol and nucleic acids 95 Finally glucose is used as a building block in the glycosylation of proteins to glycoproteins glycolipids peptidoglycans glycosides and other substances catalyzed by glycosyltransferases and can be cleaved from them by glycosidases Pathology EditDiabetes Edit Diabetes is a metabolic disorder where the body is unable to regulate levels of glucose in the blood either because of a lack of insulin in the body or the failure by cells in the body to respond properly to insulin Each of these situations can be caused by persistently high elevations of blood glucose levels through pancreatic burnout and insulin resistance The pancreas is the organ responsible for the secretion of the hormones insulin and glucagon 96 Insulin is a hormone that regulates glucose levels allowing the body s cells to absorb and use glucose Without it glucose cannot enter the cell and therefore cannot be used as fuel for the body s functions 97 If the pancreas is exposed to persistently high elevations of blood glucose levels the insulin producing cells in the pancreas could be damaged causing a lack of insulin in the body Insulin resistance occurs when the pancreas tries to produce more and more insulin in response to persistently elevated blood glucose levels Eventually the rest of the body becomes resistant to the insulin that the pancreas is producing thereby requiring more insulin to achieve the same blood glucose lowering effect and forcing the pancreas to produce even more insulin to compete with the resistance This negative spiral contributes to pancreatic burnout and the disease progression of diabetes To monitor the body s response to blood glucose lowering therapy glucose levels can be measured Blood glucose monitoring can be performed by multiple methods such as the fasting glucose test which measures the level of glucose in the blood after 8 hours of fasting Another test is the 2 hour glucose tolerance test GTT for this test the person has a fasting glucose test done then drinks a 75 gram glucose drink and is retested This test measures the ability of the person s body to process glucose Over time the blood glucose levels should decrease as insulin allows it to be taken up by cells and exit the blood stream Hypoglycemia management Edit Glucose 5 solution for infusionsIndividuals with diabetes or other conditions that result in low blood sugar often carry small amounts of sugar in various forms One sugar commonly used is glucose often in the form of glucose tablets glucose pressed into a tablet shape sometimes with one or more other ingredients as a binder hard candy or sugar packet Sources Edit Glucose tabletsMost dietary carbohydrates contain glucose either as their only building block as in the polysaccharides starch and glycogen or together with another monosaccharide as in the hetero polysaccharides sucrose and lactose 98 Unbound glucose is one of the main ingredients of honey Glucose is extremely abundant and has been isolated from a variety of natural sources across the world including male cones of the coniferous tree Wollemia nobilis in Rome 99 the roots of Ilex asprella plants in China 100 and straws from rice in California 101 Sugar content of selected common plant foods in grams per 100 g 102 Food item Carbohydrate total a including dietary fiber Total sugars Free fructose Free glucose Sucrose Ratio of fructose glucose Sucrose as proportion of total sugars FruitsApple 13 8 10 4 5 9 2 4 2 1 2 0 19 9Apricot 11 1 9 2 0 9 2 4 5 9 0 7 63 5Banana 22 8 12 2 4 9 5 0 2 4 1 0 20 0Fig dried 63 9 47 9 22 9 24 8 0 9 0 93 0 15Grapes 18 1 15 5 8 1 7 2 0 2 1 1 1Navel orange 12 5 8 5 2 25 2 0 4 3 1 1 50 4Peach 9 5 8 4 1 5 2 0 4 8 0 9 56 7Pear 15 5 9 8 6 2 2 8 0 8 2 1 8 0Pineapple 13 1 9 9 2 1 1 7 6 0 1 1 60 8Plum 11 4 9 9 3 1 5 1 1 6 0 66 16 2VegetablesBeet red 9 6 6 8 0 1 0 1 6 5 1 0 96 2Carrot 9 6 4 7 0 6 0 6 3 6 1 0 77Red pepper sweet 6 0 4 2 2 3 1 9 0 0 1 2 0 0Onion sweet 7 6 5 0 2 0 2 3 0 7 0 9 14 3Sweet potato 20 1 4 2 0 7 1 0 2 5 0 9 60 3Yam 27 9 0 5 Traces Traces Traces TracesSugar cane 13 18 0 2 1 0 0 2 1 0 11 16 1 0 highSugar beet 17 18 0 1 0 5 0 1 0 5 16 17 1 0 highGrainsCorn sweet 19 0 6 2 1 9 3 4 0 9 0 61 15 0 The carbohydrate value is calculated in the USDA database and does not always correspond to the sum of the sugars the starch and the dietary fiber Commercial production EditGlucose is produced industrially from starch by enzymatic hydrolysis using glucose amylase or by the use of acids Enzymatic hydrolysis has largely displaced acid catalyzed hydrolysis reactions 103 The result is glucose syrup enzymatically with more than 90 glucose in the dry matter 103 with an annual worldwide production volume of 20 million tonnes as of 2011 104 This is the reason for the former common name starch sugar The amylases most often come from Bacillus licheniformis 105 or Bacillus subtilis strain MN 385 105 which are more thermostable than the originally used enzymes 105 106 Starting in 1982 pullulanases from Aspergillus niger were used in the production of glucose syrup to convert amylopectin to starch amylose thereby increasing the yield of glucose 107 The reaction is carried out at a pH 4 6 5 2 and a temperature of 55 60 C 9 Corn syrup has between 20 and 95 glucose in the dry matter 108 109 The Japanese form of the glucose syrup Mizuame is made from sweet potato or rice starch 110 Maltodextrin contains about 20 glucose Many crops can be used as the source of starch Maize 103 rice 103 wheat 103 cassava 103 potato 103 barley 103 sweet potato 111 corn husk and sago are all used in various parts of the world In the United States corn starch from maize is used almost exclusively Some commercial glucose occurs as a component of invert sugar a roughly 1 1 mixture of glucose and fructose that is produced from sucrose In principle cellulose could be hydrolyzed to glucose but this process is not yet commercially practical 26 Conversion to fructose Edit Main article isoglucose In the US almost exclusively corn more precisely corn syrup is used as glucose source for the production of isoglucose which is a mixture of glucose and fructose since fructose has a higher sweetening power with same physiological calorific value of 374 kilocalories per 100 g The annual world production of isoglucose is 8 million tonnes as of 2011 104 When made from corn syrup the final product is high fructose corn syrup HFCS Commercial usage Edit Relative sweetness of various sugars in comparison with sucrose 112 Glucose is mainly used for the production of fructose and of glucose containing foods In foods it is used as a sweetener humectant to increase the volume and to create a softer mouthfeel 103 Various sources of glucose such as grape juice for wine or malt for beer are used for fermentation to ethanol during the production of alcoholic beverages Most soft drinks in the US use HFCS 55 with a fructose content of 55 in the dry mass while most other HFCS sweetened foods in the US use HFCS 42 with a fructose content of 42 in the dry mass 113 In Mexico on the other hand soft drinks are sweetened by cane sugar which has a higher sweetening power 114 In addition glucose syrup is used inter alia in the production of confectionery such as candies toffee and fondant 115 Typical chemical reactions of glucose when heated under water free conditions are caramelization and in presence of amino acids the Maillard reaction In addition various organic acids can be biotechnologically produced from glucose for example by fermentation with Clostridium thermoaceticum to produce acetic acid with Penicillium notatum for the production of araboascorbic acid with Rhizopus delemar for the production of fumaric acid with Aspergillus niger for the production of gluconic acid with Candida brumptii to produce isocitric acid with Aspergillus terreus for the production of itaconic acid with Pseudomonas fluorescens for the production of 2 ketogluconic acid with Gluconobacter suboxydans for the production of 5 ketogluconic acid with Aspergillus oryzae for the production of kojic acid with Lactobacillus delbrueckii for the production of lactic acid with Lactobacillus brevis for the production of malic acid with Propionibacter shermanii for the production of propionic acid with Pseudomonas aeruginosa for the production of pyruvic acid and with Gluconobacter suboxydans for the production of tartaric acid 116 additional citation s needed Potent bioactive natural products like triptolide that inhibit mammalian transcription via inhibition of the XPB subunit of the general transcription factor TFIIH has been recently reported as a glucose conjugate for targeting hypoxic cancer cells with increased glucose transporter expression 117 Recently glucose has been gaining commercial use as a key component of kits containing lactic acid and insulin intended to induce hypoglycemia and hyperlactatemia to combat different cancers and infections 118 Analysis EditWhen a glucose molecule is to be detected at a certain position in a larger molecule nuclear magnetic resonance spectroscopy X ray crystallography analysis or lectin immunostaining is performed with concanavalin A reporter enzyme conjugate which binds only glucose or mannose Classical qualitative detection reactions Edit These reactions have only historical significance Fehling test Edit The Fehling test is a classic method for the detection of aldoses 119 Due to mutarotation glucose is always present to a small extent as an open chain aldehyde By adding the Fehling reagents Fehling I solution and Fehling II solution the aldehyde group is oxidized to a carboxylic acid while the Cu2 tartrate complex is reduced to Cu and forms a brick red precipitate Cu2O Tollens test Edit In the Tollens test after addition of ammoniacal AgNO3 to the sample solution glucose reduces Ag to elemental silver 120 Barfoed test Edit In Barfoed s test 121 a solution of dissolved copper acetate sodium acetate and acetic acid is added to the solution of the sugar to be tested and subsequently heated in a water bath for a few minutes Glucose and other monosaccharides rapidly produce a reddish color and reddish brown copper I oxide Cu2O Nylander s test Edit As a reducing sugar glucose reacts in the Nylander s test 122 Other tests Edit See also Maillard reaction and Lye roll Upon heating a dilute potassium hydroxide solution with glucose to 100 C a strong reddish browning and a caramel like odor develops 123 Concentrated sulfuric acid dissolves dry glucose without blackening at room temperature forming sugar sulfuric acid 123 verification needed In a yeast solution alcoholic fermentation produces carbon dioxide in the ratio of 2 0454 molecules of glucose to one molecule of CO2 123 Glucose forms a black mass with stannous chloride 123 In an ammoniacal silver solution glucose as well as lactose and dextrin leads to the deposition of silver In an ammoniacal lead acetate solution white lead glycoside is formed in the presence of glucose which becomes less soluble on cooking and turns brown 123 In an ammoniacal copper solution yellow copper oxide hydrate is formed with glucose at room temperature while red copper oxide is formed during boiling same with dextrin except for with an ammoniacal copper acetate solution 123 With Hager s reagent glucose forms mercury oxide during boiling 123 An alkaline bismuth solution is used to precipitate elemental black brown bismuth with glucose 123 Glucose boiled in an ammonium molybdate solution turns the solution blue A solution with indigo carmine and sodium carbonate destains when boiled with glucose 123 Instrumental quantification Edit Refractometry and polarimetry Edit In concentrated solutions of glucose with a low proportion of other carbohydrates its concentration can be determined with a polarimeter For sugar mixtures the concentration can be determined with a refractometer for example in the Oechsle determination in the course of the production of wine Photometric enzymatic methods in solution Edit Main article Glucose oxidation reaction The enzyme glucose oxidase GOx converts glucose into gluconic acid and hydrogen peroxide while consuming oxygen Another enzyme peroxidase catalyzes a chromogenic reaction Trinder reaction 124 of phenol with 4 aminoantipyrine to a purple dye Photometric test strip method Edit The test strip method employs the above mentioned enzymatic conversion of glucose to gluconic acid to form hydrogen peroxide The reagents are immobilised on a polymer matrix the so called test strip which assumes a more or less intense color This can be measured reflectometrically at 510 nm with the aid of an LED based handheld photometer This allows routine blood sugar determination by nonscientists In addition to the reaction of phenol with 4 aminoantipyrine new chromogenic reactions have been developed that allow photometry at higher wavelengths 550 nm 750 nm 125 Amperometric glucose sensor Edit The electroanalysis of glucose is also based on the enzymatic reaction mentioned above The produced hydrogen peroxide can be amperometrically quantified by anodic oxidation at a potential of 600 mV 126 The GOx is immobilized on the electrode surface or in a membrane placed close to the electrode Precious metals such as platinum or gold are used in electrodes as well as carbon nanotube electrodes which e g are doped with boron 127 Cu CuO nanowires are also used as enzyme free amperometric electrodes reaching a detection limit of 50 mmol L 128 A particularly promising method is the so called enzyme wiring where the electron flowing during the oxidation is transferred via a molecular wire directly from the enzyme to the electrode 129 Other sensory methods Edit There are a variety of other chemical sensors for measuring glucose 130 131 Given the importance of glucose analysis in the life sciences numerous optical probes have also been developed for saccharides based on the use of boronic acids 132 which are particularly useful for intracellular sensory applications where other optical methods are not or only conditionally usable In addition to the organic boronic acid derivatives which often bind highly specifically to the 1 2 diol groups of sugars there are also other probe concepts classified by functional mechanisms which use selective glucose binding proteins e g concanavalin A as a receptor Furthermore methods were developed which indirectly detect the glucose concentration via the concentration of metabolized products e g by the consumption of oxygen using fluorescence optical sensors 133 Finally there are enzyme based concepts that use the intrinsic absorbance or fluorescence of fluorescence labeled enzymes as reporters 130 Copper iodometry Edit Glucose can be quantified by copper iodometry 134 Chromatographic methods Edit In particular for the analysis of complex mixtures containing glucose e g in honey chromatographic methods such as high performance liquid chromatography and gas chromatography 134 are often used in combination with mass spectrometry 135 136 Taking into account the isotope ratios it is also possible to reliably detect honey adulteration by added sugars with these methods 137 Derivatization using silylation reagents is commonly used 138 Also the proportions of di and trisaccharides can be quantified In vivo analysis Edit Glucose uptake in cells of organisms is measured with 2 deoxy D glucose or fluorodeoxyglucose 83 18F fluorodeoxyglucose is used as a tracer in positron emission tomography in oncology and neurology 139 where it is by far the most commonly used diagnostic agent 140 References Edit a b Boerio Goates Juliana 1991 Heat capacity measurements and thermodynamic functions of crystalline a D glucose at temperatures from 10K to 340K J Chem Thermodyn 23 5 403 09 doi 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23713 7 p 674 Wasserman D H 2009 Four grams of glucose American Journal of Physiology Endocrinology and Metabolism 296 1 E11 21 doi 10 1152 ajpendo 90563 2008 PMC 2636990 PMID 18840763 High Blood Glucose and Diabetes Complications The buildup of molecules known as AGEs may be the key link Diabetes Forecast American Diabetes Association 2010 ISSN 0095 8301 archived from the original on 2013 10 14 retrieved 2010 05 20 Essentials of Glycobiology Ajit Varki ed 2nd ed Cold Spring Harbor Laboratories Press 2009 ISBN 978 0 87969 770 9 PMID 20301239 Archived from the original on 2016 12 06 a href Template Cite book html title Template Cite book cite book a CS1 maint others link Peter C Heinrich Loffler Petrides Biochemie und Pathobiochemie Springer Verlag 2014 ISBN 978 3 642 17972 3 p 404 Harold A Harper Medizinische Biochemie Springer Verlag 2013 ISBN 978 3 662 22150 1 p 641 in German Navale A M Paranjape A N 2016 Glucose transporters Physiological and pathological roles Biophysical Reviews 8 1 5 9 doi 10 1007 s12551 015 0186 2 PMC 5425736 PMID 28510148 a b c d e f Peter C Heinrich Loffler Petrides Biochemie und Pathobiochemie Springer Verlag 2014 ISBN 978 3 642 17972 3 p 199 200 in German Thorens B 2015 GLUT2 glucose sensing and glucose homeostasis Diabetologia 58 2 221 32 doi 10 1007 s00125 014 3451 1 PMID 25421524 a b Peter C Heinrich Loffler Petrides Biochemie und Pathobiochemie Springer Verlag 2014 ISBN 978 3 642 17972 3 p 214 in German Huang S Czech M P 2007 The GLUT4 glucose transporter Cell Metabolism 5 4 237 52 doi 10 1016 j cmet 2007 03 006 PMID 17403369 Govers R 2014 Cellular regulation of glucose uptake by glucose transporter GLUT4 pp 173 240 doi 10 1016 B978 0 12 801401 1 00006 2 ISBN 9780128014011 PMID 25344989 a href Template Cite book html title Template Cite book cite book a journal ignored help Wu Xiaohua Freeze Hudson H December 2002 GLUT14 a Duplicon of GLUT3 is Specifically Expressed in Testis as Alternative Splice Forms Genomics 80 6 553 7 doi 10 1006 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