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Trehalose

February 15, 2024

Not to be confused with Trehalulose.

Trehalose (from Turkish tıgala – a sugar derived from insect cocoons + -ose)[3] is a sugar consisting of two molecules of glucose. It is also known as mycose or tremalose. Some bacteria, fungi, plants and invertebrate animals synthesize it as a source of energy, and to survive freezing and lack of water.

Trehalose
Names
IUPAC name
α-D-glucopyranosyl-(1→1)-α-D-glucopyranoside
Systematic IUPAC name
(2R,3S,4S,5R,6R)-2-(Hydroxymethyl)-6-[(2R,3R,4S,5S,6R)-3,4, 5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-3,4,5-triol
Other names
α,α‐Trehalose
Identifiers
  • 99-20-7 (anhydrous) Y
  • 6138-23-4 (dihydrate) N
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16551 Y
ChEMBL
  • ChEMBL1236395 N
ChemSpider
  • 7149 Y
ECHA InfoCard 100.002.490
  • 7427
UNII
  • B8WCK70T7I Y
  • DTXSID3048102
  • InChI=1S/C12H22O11/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1 Y
    Key: HDTRYLNUVZCQOY-LIZSDCNHSA-N Y
  • InChI=1/C12H22O11/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1
    Key: HDTRYLNUVZCQOY-LIZSDCNHBN
  • OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O1)O[C@@H]2[C@H](O)[C@@H](O)[C@H](O)[C@H](O2)CO
Properties
C12H22O11 (anhydride)
Molar mass 342.296 g/mol (anhydrous)
378.33 g/mol (dihydrate)
Appearance White orthorhombic crystals
Density 1.58 g/cm3 at 24 °C
Melting point 203 °C (397 °F; 476 K) (anhydrous)
97 °C (dihydrate)
68.9 g per 100 g at 20 °C[1]
Solubility Slightly soluble in ethanol, insoluble in diethyl ether and benzene[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Extracting trehalose was once a difficult and costly process, but around 2000, the Hayashibara company (Okayama, Japan) discovered an inexpensive extraction technology from starch.[4][5] Trehalose has high water retention capabilities, and is used in food, cosmetics and as a drug. A procedure developed in 2017 using trehalose allows sperm storage at room temperatures.[6]

Structure edit

Trehalose is a disaccharide formed by a 1,1-glycosidic bond between two α-glucose units. It is found in nature as a disaccharide and also as a monomer in some polymers.[7] Two other isomers exist, α,β-trehalose, otherwise known as neotrehalose, and β,β-trehalose (also referred to as isotrehalose). Neotrehalose has not been isolated from a living organism. Isotrehalose is also yet to be isolated from a living organism, but was found in starch hydroisolates.[7]

Synthesis edit

At least three biological pathways support trehalose biosynthesis.[7] An industrial process can derive trehalose from corn starch.[8]

Properties edit

Chemical edit

Trehalose is a nonreducing sugar formed from two glucose units joined by a 1–1 alpha bond, giving it the name α-D-glucopyranosyl-(1→1)-α-D-glucopyranoside. The bonding makes trehalose very resistant to acid hydrolysis, and therefore is stable in solution at high temperatures, even under acidic conditions. The bonding keeps nonreducing sugars in closed-ring form, such that the aldehyde or ketone end groups do not bind to the lysine or arginine residues of proteins (a process called glycation). Trehalose is less soluble than sucrose, except at high temperatures (>80 °C). Trehalose forms a rhomboid crystal as the dihydrate, and has 90% of the calorific content of sucrose in that form. Anhydrous forms of trehalose readily regain moisture to form the dihydrate. Anhydrous forms of trehalose can show interesting physical properties when heat-treated.

Trehalose aqueous solutions show a concentration-dependent clustering tendency. Owing to their ability to form hydrogen bonds, they self-associate in water to form clusters of various sizes. All-atom molecular dynamics simulations showed that concentrations of 1.5–2.2 molar allow trehalose molecular clusters to percolate and form large and continuous aggregates.[9]

Trehalose directly interacts with nucleic acids, facilitates melting of double stranded DNA and stabilizes single-stranded nucleic acids.[10]

Biological edit

Organisms ranging from bacteria, yeast, fungi, insects, invertebrates, and lower and higher plants have enzymes that can make trehalose.[7] In nature, trehalose can be found in plants, and microorganisms. In animals, trehalose is prevalent in shrimp, and also in insects, including grasshoppers, locusts, butterflies, and bees, in which trehalose serves as blood-sugar.[citation needed] Trehalase genes are found in tardigrades, the microscopic ecdysozoans found worldwide in diverse extreme environments.[11]

Trehalose is the major carbohydrate energy storage molecule used by insects for flight.[citation needed] One possible reason for this is that the glycosidic linkage of trehalose, when acted upon by an insect trehalase, releases two molecules of glucose, which is required for the rapid energy requirements of flight. This is double the efficiency of glucose release from the storage polymer starch, for which cleavage of one glycosidic linkage releases only one glucose molecule.[citation needed]

In plants, trehalose is seen in sunflower seeds, moonwort, Selaginella plants,[12] and sea algae. Within the fungi, it is prevalent in some mushrooms, such as shiitake (Lentinula edodes), oyster, king oyster, and golden needle.[13]

Even within the plant kingdom, Selaginella (sometimes called the resurrection plant), which grows in desert and mountainous areas, may be cracked and dried out, but will turn green again and revive after rain because of the function of trehalose.[12]

The two prevalent theories as to how trehalose works within the organism in the state of cryptobiosis are the vitrification theory, a state that prevents ice formation, or the water displacement theory, whereby water is replaced by trehalose.[11][14]

In bacterial cell wall, trehalose has a structural role in adaptive responses to stress such as osmotic differences and extreme temperature.[15] Yeast uses trehalose as a carbon source in response to abiotic stresses.[16] In humans, the only known function of trehalose is its ability to activate autophagy inducer.[clarification needed]

Trehalose has also been reported for anti-bacterial, anti-biofilm, and anti-inflammatory (in vitro and in vivo) activities, upon its esterification with fatty acids of varying chain lengths.[17]

Nutritional and dietary properties edit

Trehalose is rapidly broken down into glucose by the enzyme trehalase, which is present in the brush border of the intestinal mucosa of omnivores (including humans) and herbivores.[18]: 135  It causes less of a spike in blood sugar than glucose.[19] Trehalose has about 45% the sweetness of sucrose at concentrations above 22%, but when the concentration is reduced, its sweetness decreases more quickly than that of sucrose, so that a 2.3% solution tastes 6.5 times less sweet as the equivalent sugar solution.[20]: 444 

It is commonly used in prepared frozen foods, like ice cream, because it lowers the freezing point of foods.[19]

Deficiency of trehalase enzyme is unusual in humans, except in the Greenlandic Inuit, where it occurs in 10–15% of the population.[21]: 197 

Metabolism edit

Five biosynthesis pathways have been reported for trehalose. The most common pathway is TPS/TPP pathway which is used by organisms that synthesize trehalose using the enzyme trehalose-6-phosphate (T6P) synthase (TPS).[22] Second, trehalose synthase (TS) in certain types of bacteria could produce trehalose by using maltose and another disaccharide with two glucose units as substrates.[23] Third, the TreY-TreZ pathway in some bacteria converts starch that contain maltooligosaccharide or glycogen directly into trehalose.[24] Fourth, in primitive bacteria, trehalose glycisyltransferring synthase (TreT) produces trehalose from ADP-glucose and glucose.[25] Fifth, trehalose phosphorylase (TreP) either hydrolyses trehalose into glucose-1-phosphate and glucose or may act reversibly in certain species.[26] Vertebrates do not have the ability to synthesize or store trehalose.[27] Trehalase in humans is found only in specific location such as the intestinal mucosa, renal brush-border, liver and blood. Expression of this enzyme in vertebrates is initially found during the gestation period that is the highest after weaning. Then, the level of trehalase remained constant in the intestine throughout life.[28] Meanwhile, diets consisting of plants and fungi contain trehalose. Moderate amount of trehalose in diet is essential and having low amount of trehalose could result in diarrhea, or other intestinal symptoms.[29]

Medical use edit

Trehalose is an ingredient, along with hyaluronic acid, in an artificial tears product used to treat dry eye.[30][16] Outbreaks of Clostridium difficile were initially associated with trehalose,[19][31][32]. This finding was disputed in 2019.[33]

In 2021, the FDA accepted an Investigational New Drug (IND) application and granted granted fast track status for an injectable form of trehalose (SLS-005) as a potential treatment for spinocerebellar ataxia type 3 (SCA3).[34][35]

History edit

In 1832, H.A.L. Wiggers discovered trehalose in an ergot of rye,[36] and in 1859 Marcellin Berthelot isolated it from Trehala manna, a substance made by weevils and named it trehalose.[37]

Trehalose has long been known as an autophagy inducer that acts independently of mTOR.[38] In 2017, research was published showing that trehalose induces autophagy by activating TFEB,[39] a protein that acts as a master regulator of the autophagy-lysosome pathway.[40]

See also edit

References edit

  1. ^ Higashiyama T (2002). "Novel functions and applications of trehalose" (PDF). Pure Appl. Chem. 74 (7): 1263–1269. doi:10.1351/pac200274071263. S2CID 28311022.
  2. ^ Lide, David R. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, Florida: CRC Press. pp. 3–534. ISBN 978-0-8493-0594-8.
  3. ^ . Archived from the original on February 26, 2022.
  4. ^ Cargill, Incorporated (30 May 2011). "Cargill, Hayashibara to Introduce Trehalose Sweetener to the Americas". PR Newswire. Retrieved 2011-07-31.
  5. ^ "JAPAN: Cargill, Hayashibara to Introduce Trehalose Sweetener to the Americas". just-food.com. 2000-05-31. Retrieved 2 February 2013.
  6. ^ Patrick, Jennifer L.; Elliott, Gloria D.; Comizzoli, Pierre (1 November 2017). "Structural integrity and developmental potential of spermatozoa following microwave-assisted drying in the domestic cat model". Theriogenology. 103: 36–43. doi:10.1016/j.theriogenology.2017.07.037. PMID 28772113.
  7. ^ a b c d Elbein AD, Pan YT, Pastuszak I, Carroll D (April 2003). "New insights on trehalose: a multifunctional molecule". Glycobiology. 13 (4): 17R–27R. doi:10.1093/glycob/cwg047. PMID 12626396.
  8. ^ [dead link]"GRAS Notification for Hayashibara Trehalose" (PDF). Food and Drug Administration. May 3, 2000: 10. {{cite journal}}: Cite journal requires |journal= (help)
  9. ^ Sapir L, Harries D (February 2011). "Linking trehalose self-association with binary aqueous solution equation of state". The Journal of Physical Chemistry B. 115 (4): 624–34. doi:10.1021/jp109780n. PMID 21186829.
  10. ^ Bezrukavnikov S, Mashaghi A, van Wijk RJ, Gu C, Yang LJ, Gao YQ, Tans SJ (October 2014). "Trehalose facilitates DNA melting: a single-molecule optical tweezers study". Soft Matter. 10 (37): 7269–77. Bibcode:2014SMat...10.7269B. doi:10.1039/C4SM01532K. PMID 25096217.
  11. ^ a b Kamilari, Maria; Jørgensen, Aslak; Schiøtt, Morten; Møbjerg, Nadja (2019-07-24). "Comparative transcriptomics suggest unique molecular adaptations within tardigrade lineages". BMC Genomics. 20 (1): 607. doi:10.1186/s12864-019-5912-x. ISSN 1471-2164. PMC 6652013. PMID 31340759.
  12. ^ a b Zentella R, Mascorro-Gallardo JO, Van Dijck P, Folch-Mallol J, Bonini B, Van Vaeck C, Gaxiola R, Covarrubias AA, Nieto-Sotelo J, Thevelein JM, Iturriaga G (April 1999). "A Selaginella lepidophylla trehalose-6-phosphate synthase complements growth and stress-tolerance defects in a yeast tps1 mutant". Plant Physiology. 119 (4): 1473–82. doi:10.1104/pp.119.4.1473. PMC 32033. PMID 10198107.
  13. ^ Reis FS, Barros L, Martins A, Ferreira IC (February 2012). "Chemical composition and nutritional value of the most widely appreciated cultivated mushrooms: an inter-species comparative study" (PDF). Food and Chemical Toxicology. 50 (2): 191–7. doi:10.1016/j.fct.2011.10.056. hdl:10198/7341. PMID 22056333. S2CID 23997767.
  14. ^ Sola-Penna M, Meyer-Fernandes JR (December 1998). "Stabilization against thermal inactivation promoted by sugars on enzyme structure and function: why is trehalose more effective than other sugars?". Archives of Biochemistry and Biophysics. 360 (1): 10–4. doi:10.1006/abbi.1998.0906. PMID 9826423.
  15. ^ Iturriaga, Gabriel; Suárez, Ramón; Nova-Franco, Barbara (2009). "Trehalose Metabolism: From Osmoprotection to Signaling". International Journal of Molecular Sciences. 10 (9): 3793–3810. doi:10.3390/ijms10093793. PMC 2769160. PMID 19865519.
  16. ^ a b Pucker AD, Ng SM, Nichols JJ (February 2016). "Over the counter (OTC) artificial tear drops for dry eye syndrome". The Cochrane Database of Systematic Reviews. 2016 (2): CD009729. doi:10.1002/14651858.CD009729.pub2. PMC 5045033. PMID 26905373.
  17. ^ Marathe, Sandesh J.; Shah, Nirali N.; Singhal, Rekha S. (2020-01-01). "Enzymatic synthesis of fatty acid esters of trehalose: Process optimization, characterization of the esters and evaluation of their bioactivities". Bioorganic Chemistry. 94: 103460. doi:10.1016/j.bioorg.2019.103460. ISSN 0045-2068. PMID 31791682. S2CID 208610507.
  18. ^ Mathlouthi, M., ed. (1999). Food packaging and preservation. Gaithersburg, Md.: Aspen Publishers. ISBN 978-0-8342-1349-4. Retrieved 25 June 2014.
  19. ^ a b c Collins F (9 January 2018). "Has an Alternative to Table Sugar Contributed to the C. Diff. Epidemic?". NIH Director's Blog.
  20. ^ O'Brien-Nabors, Lyn, ed. (2012). Alternative sweeteners (4th ed.). Boca Raton: CRC Press. ISBN 978-1-4398-4614-8. Retrieved 25 June 2014.
  21. ^ Kohlmeier M (2003). Nutrient Metabolism. Burlington: Elsevier. ISBN 978-0-08-053789-4. Retrieved 25 June 2014.
  22. ^ Cabib, E.; Leloir, L. F. (1958). "The biosynthesis of trehalose phosphate". The Journal of Biological Chemistry. 231 (1): 259–275. doi:10.1016/S0021-9258(19)77303-7. hdl:11336/135983. ISSN 0021-9258. PMID 13538966.
  23. ^ Nishimoto, T.; Nakano, M.; Nakada, T.; Chaen, H.; Fukuda, S.; Sugimoto, T.; Kurimoto, M.; Tsujisaka, Y. (April 1996). "Purification and properties of a novel enzyme, trehalose synthase, from Pimelobacter sp. R48". Bioscience, Biotechnology, and Biochemistry. 60 (4): 640–644. doi:10.1271/bbb.60.640. ISSN 0916-8451. PMID 8829531.
  24. ^ Maruta, Kazuhiko; Mitsuzumi, Hitoshi; Nakada, Tetsuya; Kubota, Michio; Chaen, Hiroto; Fukuda, Shigeharu; Sugimoto, Toshiyuki; Kurimoto, Masashi (1996-12-06). "Cloning and sequencing of a cluster of genes encoding novel enzymes of trehalose biosynthesis from thermophilic archaebacterium Sulfolobus acidocaldarius". Biochimica et Biophysica Acta (BBA) - General Subjects. 1291 (3): 177–181. doi:10.1016/S0304-4165(96)00082-7. ISSN 0304-4165. PMID 8980629.
  25. ^ Qu, Qiuhao; Lee, Sung-Jae; Boos, Winfried (2004-11-12). "TreT, a Novel Trehalose Glycosyltransferring Synthase of the Hyperthermophilic Archaeon Thermococcus litoralis*". Journal of Biological Chemistry. 279 (46): 47890–47897. doi:10.1074/jbc.M404955200. ISSN 0021-9258. PMID 15364950.
  26. ^ Ren, Yuanyuan; Dai, Xiuyu; Zhou, Jian; Liu, Jingfang; Pei, Huadong; Xiang, Hua (2005-05-01). "Gene expression and molecular characterization of a thermostable trehalose phosphorylase fromThermoanaerobacter tengcongensis". Science in China Series C: Life Sciences. 48 (3): 221–227. doi:10.1007/BF03183615. ISSN 1862-2798. PMID 16092754. S2CID 23443429.
  27. ^ Elbein, Alan D. (1974-01-01), Tipson, R. Stuart; Horton, Derek (eds.), "The Metabolism of α,α-Trehalose**The work cited from the author's laboratory was supported by grants from the Robert A. Welch Foundation and the National Institutes of Health (AI 09402).", Advances in Carbohydrate Chemistry and Biochemistry, Academic Press, 30: 227–256, doi:10.1016/S0065-2318(08)60266-8, PMID 4377836, retrieved 2021-11-30
  28. ^ Galand, G. (1989). "Brush border membrane sucrase-isomaltase, maltase-glucoamylase and trehalase in mammals. Comparative development, effects of glucocorticoids, molecular mechanisms, and phylogenetic implications". Comparative Biochemistry and Physiology. B, Comparative Biochemistry. 94 (1): 1–11. doi:10.1016/0305-0491(89)90002-3. ISSN 0305-0491. PMID 2513162.
  29. ^ Thevelein, J M (March 1984). "Regulation of trehalose mobilization in fungi". Microbiological Reviews. 48 (1): 42–59. doi:10.1128/mr.48.1.42-59.1984. ISSN 0146-0749. PMC 373002. PMID 6325857.
  30. ^ Pinto-Bonilla JC, Del Olmo-Jimeno A, Llovet-Osuna F, Hernández-Galilea E (2015). "A randomized crossover study comparing trehalose/hyaluronate eyedrops and standard treatment: patient satisfaction in the treatment of dry eye syndrome". Therapeutics and Clinical Risk Management. 11: 595–603. doi:10.2147/TCRM.S77091. PMC 4403513. PMID 25926736.
  31. ^ Ballard JD (January 2018). "Pathogens boosted by food additive". Nature. 553 (7688): 285–286. doi:10.1038/d41586-017-08775-4. PMID 29345660.
  32. ^ Collins J, Robinson C, Danhof H, Knetsch CW, van Leeuwen HC, Lawley TD, Auchtung JM, Britton RA (January 2018). "Dietary trehalose enhances virulence of epidemic Clostridium difficile". Nature. 553 (7688): 291–294. Bibcode:2018Natur.553..291C. doi:10.1038/nature25178. PMC 5984069. PMID 29310122.
  33. ^ Eyre, David W.; Didelot, Xavier; Buckley, Anthony M.; Freeman, Jane; Moura, Ines B.; Crook, Derrick W.; Peto, Tim E.A.; Walker, A. Sarah; Wilcox, Mark H.; Dingle, Kate E. (2019). "Clostridium difficile trehalose metabolism variants are common and not associated with adverse patient outcomes when variably present in the same lineage". eBioMedicine. 43: 347–355. doi:10.1016/j.ebiom.2019.04.038. ISSN 2352-3964. PMC 6558026. PMID 31036529.
  34. ^ Park, Brian (8 November 2021). "Trehalose Fast Tracked for Spinocerebellar Ataxia". MPR. Retrieved 14 November 2023.
  35. ^ "FDA Accepts Investigational New Drug Application and Grants Fast Track Designation of Trehalose for Spinocerebellar Ataxia Treatment". Practical Neurology. 12 November 2021. Retrieved 14 November 2023.
  36. ^ Wiggers HA (1832). "Untersuchung über das Mutterkorn, Secale cornutum". Annalen der Pharmacie. 1 (2): 129–182. doi:10.1002/jlac.18320010202.
  37. ^ Tillequin F (July 2009). "Le Tréhala, une drogue à la croisée des chemins" [Trehala, a meeting point between zoology, botany, chemistry, and biochemistry]. Revue d'Histoire de la Pharmacie (in French). 57 (362): 163–72. doi:10.3406/pharm.2009.22043. PMID 20027793.
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External links edit

  •   Media related to Trehalose at Wikimedia Commons
  • Trehalose in sperm preservation

February 15, 2024
trehalose, confused, with, trehalulose, from, turkish, tıgala, sugar, derived, from, insect, cocoons, sugar, consisting, molecules, glucose, also, known, mycose, tremalose, some, bacteria, fungi, plants, invertebrate, animals, synthesize, source, energy, survi. Not to be confused with Trehalulose Trehalose from Turkish tigala a sugar derived from insect cocoons ose 3 is a sugar consisting of two molecules of glucose It is also known as mycose or tremalose Some bacteria fungi plants and invertebrate animals synthesize it as a source of energy and to survive freezing and lack of water Trehalose NamesIUPAC name a D glucopyranosyl 1 1 a D glucopyranosideSystematic IUPAC name 2R 3S 4S 5R 6R 2 Hydroxymethyl 6 2R 3R 4S 5S 6R 3 4 5 trihydroxy 6 hydroxymethyl oxan 2 yl oxyoxane 3 4 5 triolOther names a a TrehaloseIdentifiersCAS Number 99 20 7 anhydrous Y6138 23 4 dihydrate N3D model JSmol Interactive imageChEBI CHEBI 16551 YChEMBL ChEMBL1236395 NChemSpider 7149 YECHA InfoCard 100 002 490PubChem CID 7427UNII B8WCK70T7I YCompTox Dashboard EPA DTXSID3048102InChI InChI 1S C12H22O11 c13 1 3 5 15 7 17 9 19 11 21 3 23 12 10 20 8 18 6 16 4 2 14 22 12 h3 20H 1 2H2 t3 4 5 6 7 8 9 10 11 12 m1 s1 YKey HDTRYLNUVZCQOY LIZSDCNHSA N YInChI 1 C12H22O11 c13 1 3 5 15 7 17 9 19 11 21 3 23 12 10 20 8 18 6 16 4 2 14 22 12 h3 20H 1 2H2 t3 4 5 6 7 8 9 10 11 12 m1 s1Key HDTRYLNUVZCQOY LIZSDCNHBNSMILES OC C H 1 C H O C H O C H O C H O1 O C H 2 C H O C H O C H O C H O2 COPropertiesChemical formula C12H22O11 anhydride Molar mass 342 296 g mol anhydrous 378 33 g mol dihydrate Appearance White orthorhombic crystalsDensity 1 58 g cm3 at 24 CMelting point 203 C 397 F 476 K anhydrous 97 C dihydrate Solubility in water 68 9 g per 100 g at 20 C 1 Solubility Slightly soluble in ethanol insoluble in diethyl ether and benzene 2 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Extracting trehalose was once a difficult and costly process but around 2000 the Hayashibara company Okayama Japan discovered an inexpensive extraction technology from starch 4 5 Trehalose has high water retention capabilities and is used in food cosmetics and as a drug A procedure developed in 2017 using trehalose allows sperm storage at room temperatures 6 Contents 1 Structure 2 Synthesis 3 Properties 3 1 Chemical 3 2 Biological 4 Nutritional and dietary properties 5 Metabolism 6 Medical use 7 History 8 See also 9 References 10 External linksStructure editTrehalose is a disaccharide formed by a 1 1 glycosidic bond between two a glucose units It is found in nature as a disaccharide and also as a monomer in some polymers 7 Two other isomers exist a b trehalose otherwise known as neotrehalose and b b trehalose also referred to as isotrehalose Neotrehalose has not been isolated from a living organism Isotrehalose is also yet to be isolated from a living organism but was found in starch hydroisolates 7 Synthesis editAt least three biological pathways support trehalose biosynthesis 7 An industrial process can derive trehalose from corn starch 8 Properties editChemical edit Trehalose is a nonreducing sugar formed from two glucose units joined by a 1 1 alpha bond giving it the name a D glucopyranosyl 1 1 a D glucopyranoside The bonding makes trehalose very resistant to acid hydrolysis and therefore is stable in solution at high temperatures even under acidic conditions The bonding keeps nonreducing sugars in closed ring form such that the aldehyde or ketone end groups do not bind to the lysine or arginine residues of proteins a process called glycation Trehalose is less soluble than sucrose except at high temperatures gt 80 C Trehalose forms a rhomboid crystal as the dihydrate and has 90 of the calorific content of sucrose in that form Anhydrous forms of trehalose readily regain moisture to form the dihydrate Anhydrous forms of trehalose can show interesting physical properties when heat treated Trehalose aqueous solutions show a concentration dependent clustering tendency Owing to their ability to form hydrogen bonds they self associate in water to form clusters of various sizes All atom molecular dynamics simulations showed that concentrations of 1 5 2 2 molar allow trehalose molecular clusters to percolate and form large and continuous aggregates 9 Trehalose directly interacts with nucleic acids facilitates melting of double stranded DNA and stabilizes single stranded nucleic acids 10 Biological edit Organisms ranging from bacteria yeast fungi insects invertebrates and lower and higher plants have enzymes that can make trehalose 7 In nature trehalose can be found in plants and microorganisms In animals trehalose is prevalent in shrimp and also in insects including grasshoppers locusts butterflies and bees in which trehalose serves as blood sugar citation needed Trehalase genes are found in tardigrades the microscopic ecdysozoans found worldwide in diverse extreme environments 11 Trehalose is the major carbohydrate energy storage molecule used by insects for flight citation needed One possible reason for this is that the glycosidic linkage of trehalose when acted upon by an insect trehalase releases two molecules of glucose which is required for the rapid energy requirements of flight This is double the efficiency of glucose release from the storage polymer starch for which cleavage of one glycosidic linkage releases only one glucose molecule citation needed In plants trehalose is seen in sunflower seeds moonwort Selaginella plants 12 and sea algae Within the fungi it is prevalent in some mushrooms such as shiitake Lentinula edodes oyster king oyster and golden needle 13 Even within the plant kingdom Selaginella sometimes called the resurrection plant which grows in desert and mountainous areas may be cracked and dried out but will turn green again and revive after rain because of the function of trehalose 12 The two prevalent theories as to how trehalose works within the organism in the state of cryptobiosis are the vitrification theory a state that prevents ice formation or the water displacement theory whereby water is replaced by trehalose 11 14 In bacterial cell wall trehalose has a structural role in adaptive responses to stress such as osmotic differences and extreme temperature 15 Yeast uses trehalose as a carbon source in response to abiotic stresses 16 In humans the only known function of trehalose is its ability to activate autophagy inducer clarification needed Trehalose has also been reported for anti bacterial anti biofilm and anti inflammatory in vitro and in vivo activities upon its esterification with fatty acids of varying chain lengths 17 Nutritional and dietary properties editTrehalose is rapidly broken down into glucose by the enzyme trehalase which is present in the brush border of the intestinal mucosa of omnivores including humans and herbivores 18 135 It causes less of a spike in blood sugar than glucose 19 Trehalose has about 45 the sweetness of sucrose at concentrations above 22 but when the concentration is reduced its sweetness decreases more quickly than that of sucrose so that a 2 3 solution tastes 6 5 times less sweet as the equivalent sugar solution 20 444 It is commonly used in prepared frozen foods like ice cream because it lowers the freezing point of foods 19 Deficiency of trehalase enzyme is unusual in humans except in the Greenlandic Inuit where it occurs in 10 15 of the population 21 197 Metabolism editFive biosynthesis pathways have been reported for trehalose The most common pathway is TPS TPP pathway which is used by organisms that synthesize trehalose using the enzyme trehalose 6 phosphate T6P synthase TPS 22 Second trehalose synthase TS in certain types of bacteria could produce trehalose by using maltose and another disaccharide with two glucose units as substrates 23 Third the TreY TreZ pathway in some bacteria converts starch that contain maltooligosaccharide or glycogen directly into trehalose 24 Fourth in primitive bacteria trehalose glycisyltransferring synthase TreT produces trehalose from ADP glucose and glucose 25 Fifth trehalose phosphorylase TreP either hydrolyses trehalose into glucose 1 phosphate and glucose or may act reversibly in certain species 26 Vertebrates do not have the ability to synthesize or store trehalose 27 Trehalase in humans is found only in specific location such as the intestinal mucosa renal brush border liver and blood Expression of this enzyme in vertebrates is initially found during the gestation period that is the highest after weaning Then the level of trehalase remained constant in the intestine throughout life 28 Meanwhile diets consisting of plants and fungi contain trehalose Moderate amount of trehalose in diet is essential and having low amount of trehalose could result in diarrhea or other intestinal symptoms 29 Medical use editTrehalose is an ingredient along with hyaluronic acid in an artificial tears product used to treat dry eye 30 16 Outbreaks of Clostridium difficile were initially associated with trehalose 19 31 32 This finding was disputed in 2019 33 In 2021 the FDA accepted an Investigational New Drug IND application and granted granted fast track status for an injectable form of trehalose SLS 005 as a potential treatment for spinocerebellar ataxia type 3 SCA3 34 35 History editIn 1832 H A L Wiggers discovered trehalose in an ergot of rye 36 and in 1859 Marcellin Berthelot isolated it from Trehala manna a substance made by weevils and named it trehalose 37 Trehalose has long been known as an autophagy inducer that acts independently of mTOR 38 In 2017 research was published showing that trehalose induces autophagy by activating TFEB 39 a protein that acts as a master regulator of the autophagy lysosome pathway 40 See also editBiostasis Cryoprotectant Cryptobiosis Freeze drying Lentztrehalose TrehalosamineReferences edit Higashiyama T 2002 Novel functions and applications of trehalose PDF Pure Appl Chem 74 7 1263 1269 doi 10 1351 pac200274071263 S2CID 28311022 Lide David R 1998 Handbook of Chemistry and Physics 87 ed Boca Raton Florida CRC Press pp 3 534 ISBN 978 0 8493 0594 8 Trehalose Definition of Trehalose by Lexico Archived from the original on February 26 2022 Cargill Incorporated 30 May 2011 Cargill Hayashibara to Introduce Trehalose Sweetener to the Americas PR Newswire Retrieved 2011 07 31 JAPAN Cargill Hayashibara to Introduce Trehalose Sweetener to the Americas just food com 2000 05 31 Retrieved 2 February 2013 Patrick Jennifer L Elliott Gloria D Comizzoli Pierre 1 November 2017 Structural integrity and developmental potential of spermatozoa following microwave assisted drying in the domestic cat model Theriogenology 103 36 43 doi 10 1016 j theriogenology 2017 07 037 PMID 28772113 a b c d Elbein AD Pan YT Pastuszak I Carroll D April 2003 New insights on trehalose a multifunctional molecule Glycobiology 13 4 17R 27R doi 10 1093 glycob cwg047 PMID 12626396 dead link GRAS Notification for Hayashibara Trehalose PDF Food and Drug Administration May 3 2000 10 a href Template Cite journal html title Template Cite journal cite journal a Cite journal requires journal help Sapir L Harries D February 2011 Linking trehalose self association with binary aqueous solution equation of state The Journal of Physical Chemistry B 115 4 624 34 doi 10 1021 jp109780n PMID 21186829 Bezrukavnikov S Mashaghi A van Wijk RJ Gu C Yang LJ Gao YQ Tans SJ October 2014 Trehalose facilitates DNA melting a single molecule optical tweezers study Soft Matter 10 37 7269 77 Bibcode 2014SMat 10 7269B doi 10 1039 C4SM01532K PMID 25096217 a b Kamilari Maria Jorgensen Aslak Schiott Morten Mobjerg Nadja 2019 07 24 Comparative transcriptomics suggest unique molecular adaptations within tardigrade lineages BMC Genomics 20 1 607 doi 10 1186 s12864 019 5912 x ISSN 1471 2164 PMC 6652013 PMID 31340759 a b Zentella R Mascorro Gallardo JO Van Dijck P Folch Mallol J Bonini B Van Vaeck C Gaxiola R Covarrubias AA Nieto Sotelo J Thevelein JM Iturriaga G April 1999 A Selaginella lepidophylla trehalose 6 phosphate synthase complements growth and stress tolerance defects in a yeast tps1 mutant Plant Physiology 119 4 1473 82 doi 10 1104 pp 119 4 1473 PMC 32033 PMID 10198107 Reis FS Barros L Martins A Ferreira IC February 2012 Chemical composition and nutritional value of the most widely appreciated cultivated mushrooms an inter species comparative study PDF Food and Chemical Toxicology 50 2 191 7 doi 10 1016 j fct 2011 10 056 hdl 10198 7341 PMID 22056333 S2CID 23997767 Sola Penna M Meyer Fernandes JR December 1998 Stabilization against thermal inactivation promoted by sugars on enzyme structure and function why is trehalose more effective than other sugars Archives of Biochemistry and Biophysics 360 1 10 4 doi 10 1006 abbi 1998 0906 PMID 9826423 Iturriaga Gabriel Suarez Ramon Nova Franco Barbara 2009 Trehalose Metabolism From Osmoprotection to Signaling International Journal of Molecular Sciences 10 9 3793 3810 doi 10 3390 ijms10093793 PMC 2769160 PMID 19865519 a b Pucker AD Ng SM Nichols JJ February 2016 Over the counter OTC artificial tear drops for dry eye syndrome The Cochrane Database of Systematic Reviews 2016 2 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77303 7 hdl 11336 135983 ISSN 0021 9258 PMID 13538966 Nishimoto T Nakano M Nakada T Chaen H Fukuda S Sugimoto T Kurimoto M Tsujisaka Y April 1996 Purification and properties of a novel enzyme trehalose synthase from Pimelobacter sp R48 Bioscience Biotechnology and Biochemistry 60 4 640 644 doi 10 1271 bbb 60 640 ISSN 0916 8451 PMID 8829531 Maruta Kazuhiko Mitsuzumi Hitoshi Nakada Tetsuya Kubota Michio Chaen Hiroto Fukuda Shigeharu Sugimoto Toshiyuki Kurimoto Masashi 1996 12 06 Cloning and sequencing of a cluster of genes encoding novel enzymes of trehalose biosynthesis from thermophilic archaebacterium Sulfolobus acidocaldarius Biochimica et Biophysica Acta BBA General Subjects 1291 3 177 181 doi 10 1016 S0304 4165 96 00082 7 ISSN 0304 4165 PMID 8980629 Qu Qiuhao Lee Sung Jae Boos Winfried 2004 11 12 TreT a Novel Trehalose Glycosyltransferring Synthase of the Hyperthermophilic Archaeon Thermococcus litoralis Journal of Biological Chemistry 279 46 47890 47897 doi 10 1074 jbc M404955200 ISSN 0021 9258 PMID 15364950 Ren Yuanyuan Dai Xiuyu Zhou Jian Liu Jingfang Pei Huadong Xiang Hua 2005 05 01 Gene expression and molecular characterization of a thermostable trehalose phosphorylase fromThermoanaerobacter tengcongensis Science in China Series C Life Sciences 48 3 221 227 doi 10 1007 BF03183615 ISSN 1862 2798 PMID 16092754 S2CID 23443429 Elbein Alan D 1974 01 01 Tipson R Stuart Horton Derek eds The Metabolism of a a Trehalose The work cited from the author s laboratory was supported by grants from the Robert A Welch Foundation and the National Institutes of Health AI 09402 Advances in Carbohydrate Chemistry and Biochemistry Academic Press 30 227 256 doi 10 1016 S0065 2318 08 60266 8 PMID 4377836 retrieved 2021 11 30 Galand G 1989 Brush border membrane sucrase isomaltase maltase glucoamylase and trehalase in mammals Comparative development effects of glucocorticoids molecular mechanisms and phylogenetic implications Comparative Biochemistry and Physiology B Comparative Biochemistry 94 1 1 11 doi 10 1016 0305 0491 89 90002 3 ISSN 0305 0491 PMID 2513162 Thevelein J M March 1984 Regulation of trehalose mobilization in fungi Microbiological Reviews 48 1 42 59 doi 10 1128 mr 48 1 42 59 1984 ISSN 0146 0749 PMC 373002 PMID 6325857 Pinto Bonilla JC Del Olmo Jimeno A Llovet Osuna F Hernandez Galilea E 2015 A randomized crossover study comparing trehalose hyaluronate eyedrops and standard treatment patient satisfaction in the treatment of dry eye syndrome Therapeutics and Clinical Risk Management 11 595 603 doi 10 2147 TCRM S77091 PMC 4403513 PMID 25926736 Ballard JD January 2018 Pathogens boosted by food additive Nature 553 7688 285 286 doi 10 1038 d41586 017 08775 4 PMID 29345660 Collins J Robinson C Danhof H Knetsch CW van Leeuwen HC Lawley TD Auchtung JM Britton RA January 2018 Dietary trehalose enhances virulence of epidemic Clostridium difficile Nature 553 7688 291 294 Bibcode 2018Natur 553 291C doi 10 1038 nature25178 PMC 5984069 PMID 29310122 Eyre David W Didelot Xavier Buckley Anthony M Freeman Jane Moura Ines B Crook Derrick W Peto Tim E A Walker A Sarah Wilcox Mark H Dingle Kate E 2019 Clostridium difficile trehalose metabolism variants are common and not associated with adverse patient outcomes when variably present in the same lineage eBioMedicine 43 347 355 doi 10 1016 j ebiom 2019 04 038 ISSN 2352 3964 PMC 6558026 PMID 31036529 Park Brian 8 November 2021 Trehalose Fast Tracked for Spinocerebellar Ataxia MPR Retrieved 14 November 2023 FDA Accepts Investigational New Drug Application and Grants Fast Track Designation of Trehalose for Spinocerebellar Ataxia Treatment Practical Neurology 12 November 2021 Retrieved 14 November 2023 Wiggers HA 1832 Untersuchung uber das Mutterkorn Secale cornutum Annalen der Pharmacie 1 2 129 182 doi 10 1002 jlac 18320010202 Tillequin F July 2009 Le Trehala une drogue a la croisee des chemins Trehala a meeting point between zoology botany chemistry and biochemistry Revue d Histoire de la Pharmacie in French 57 362 163 72 doi 10 3406 pharm 2009 22043 PMID 20027793 Menzies FM Fleming A Rubinsztein DC June 2015 Compromised autophagy and neurodegenerative diseases Nature Reviews Neuroscience 16 6 345 57 doi 10 1038 nrn3961 PMID 25991442 S2CID 19272817 Sharma J di Ronza A Lotfi P Sardiello M July 2018 Lysosomes and Brain Health Annual Review of Neuroscience 41 255 276 doi 10 1146 annurev neuro 080317 061804 PMID 29661037 S2CID 207581692 Sardiello M May 2016 Transcription factor EB from master coordinator of lysosomal pathways to candidate therapeutic target in degenerative storage diseases Annals of the New York Academy of Sciences 1371 1 3 14 Bibcode 2016NYASA1371 3S doi 10 1111 nyas 13131 PMC 5032832 PMID 27299292 External links edit nbsp Media related to Trehalose at Wikimedia Commons Trehalose in sperm preservation Retrieved from https en wikipedia org w index php title Trehalose amp oldid 1193573471, wikipedia, wiki, book, books, library,

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