fbpx
Wikipedia

Inosinic acid

Inosinic acid or inosine monophosphate (IMP) is a nucleotide (that is, a nucleoside monophosphate). Widely used as a flavor enhancer, it is typically obtained from chicken byproducts or other meat industry waste. Inosinic acid is important in metabolism. It is the ribonucleotide of hypoxanthine and the first nucleotide formed during the synthesis of purine nucleotides. It can also be formed by the deamination of adenosine monophosphate by AMP deaminase. It can be hydrolysed to inosine.

Inosinic acid
Names
IUPAC name
5'-Inosinic acid
Other names
IMP,
Hypoxanthine ribotide
Identifiers
  • 131-99-7 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17202 Y
ChEMBL
  • ChEMBL1233478 N
ChemSpider
  • 8264 Y
ECHA InfoCard 100.004.588
E number E630 (flavour enhancer)
  • 5124
MeSH Inosine+monophosphate
  • 8582
UNII
  • TAO7US05G5 Y
  • DTXSID4044294
  • InChI=1S/C10H13N4O8P/c15-6-4(1-21-23(18,19)20)22-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17/h2-4,6-7,10,15-16H,1H2,(H,11,12,17)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1 Y
    Key: GRSZFWQUAKGDAV-KQYNXXCUSA-N Y
  • InChI=1/C10H13N4O8P/c15-6-4(1-21-23(18,19)20)22-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17/h2-4,6-7,10,15-16H,1H2,(H,11,12,17)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
    Key: GRSZFWQUAKGDAV-KQYNXXCUBU
  • O=C3/N=C\Nc1c3ncn1[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)COP(=O)(O)O
Properties
C10H13N4O8P
Molar mass 348.208 g·mol−1
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 ?)

The enzyme deoxyribonucleoside triphosphate pyrophosphohydrolase, encoded by YJR069C in Saccharomyces cerevisiae and containing (d)ITPase and (d)XTPase activities, hydrolyzes inosine triphosphate (ITP) releasing pyrophosphate and IMP.[1]

Important derivatives of inosinic acid include the purine nucleotides found in nucleic acids and adenosine triphosphate, which is used to store chemical energy in muscle and other tissues.

In the food industry, inosinic acid and its salts such as disodium inosinate are used as flavor enhancers. It is known as E number reference E630.

Inosinate synthesis edit

The inosinate synthesis is complex, beginning with a 5-phosphoribosyl-1-pyrophosphate (PRPP). Enzymes taking part in IMP synthesis constitute a multienzyme complex in the cell. Evidence demonstrates that there are multifunctional enzymes, and some of them catalyze non-sequential steps in the pathway.[citation needed]

 
This figure shows the pathway described: IMP synthesis.

Synthesis of other purine nucleotides edit

Within a few steps inosinate becomes AMP or GMP.[2] Both compounds are RNA nucleotides.[2] AMP differs from inosinate by the replacement of IMP's carbon-6 carbonyl with an amino group. The interconversion of AMP and IMP occurs as part of the purine nucleotide cycle.[3] GMP is formed by the inosinate oxidation to xanthylate (XMP), and afterwards adds an amino group on carbon 2. Hydrogen acceptor on inosinate oxidation is NAD+. Finally, carbon 2 gains the amino group by spending an ATP molecule (which becomes AMP+2Pi). While AMP synthesis requires GTP, GMP synthesis uses ATP. That difference offers an important regulation possibility.

 
Glutamine-PRPP-amidotransferase

Regulation of purine nucleotide biosynthesis edit

Inosinate and many other molecules inhibit the synthesis of 5-phosphoribosylamine from 5-phosphoribosyl-1-pyrophosphate (PRPP), disabling the enzyme that catalyzes the reaction: glutamine-5-phosphoribosyl-1-pyrophosphate-amidotransferase. In other words, when levels of inosinate are high, glutamine-5-phosphoribosyl-1-pyrophosphate-amidotransferase is inhibited, and, as a consequence, inosinate levels decrease. Also, as a result, adenylate and guanylate are not produced, which means that RNA synthesis cannot be completed because of the lack of these two important RNA nucleotides.

Applications edit

Inosinic acid can be converted into various salts including disodium inosinate (E631), dipotassium inosinate (E632), and calcium inosinate (E633). These three compounds are used as flavor enhancers for the basic taste umami or savoriness with a comparatively high effectiveness. They are mostly used in soups, sauces, and seasonings for the intensification and balance of the flavor of meat.

See also edit

References edit

  1. ^ Davies O, Mendes P, Smallbone K, Malys N (2012). "Characterisation of multiple substrate-specific (d)ITP/(d)XTPase and modelling of deaminated purine nucleotide metabolism". BMB Reports. 45 (4): 259–64. doi:10.5483/BMBRep.2012.45.4.259. PMID 22531138.
  2. ^ a b Mader, M. M.; Henry, J. R. (2007-01-01), Taylor, John B.; Triggle, David J. (eds.), "7.03 - Antimetabolites", Comprehensive Medicinal Chemistry II, Oxford: Elsevier, pp. 55–79, doi:10.1016/b0-08-045044-x/00204-2, ISBN 978-0-08-045044-5, retrieved 2020-12-17
  3. ^ Voet, D, Voet, J. G., Biochemistry (3rd Edition), John Wiley & Sons, Inc., 2004, pg 1095

Further reading edit

  • Berg, Jeremy M.; Bioquímica; Editorial Reverté; 6ena edició; Barcelona 2007.
  • Nelson, David L.; Principles of biochemistry; Editorial W.H Freeman and Company; 4th edition; New York 2005.

inosinic, acid, e630, redirects, here, locomotive, Čsd, class, this, article, needs, additional, citations, verification, please, help, improve, this, article, adding, citations, reliable, sources, unsourced, material, challenged, removed, find, sources, news,. E630 redirects here For the locomotive E 630 see CSD Class E 499 3 E 630 This article needs additional citations for verification Please help improve this article by adding citations to reliable sources Unsourced material may be challenged and removed Find sources Inosinic acid news newspapers books scholar JSTOR November 2014 Learn how and when to remove this template message Inosinic acid or inosine monophosphate IMP is a nucleotide that is a nucleoside monophosphate Widely used as a flavor enhancer it is typically obtained from chicken byproducts or other meat industry waste Inosinic acid is important in metabolism It is the ribonucleotide of hypoxanthine and the first nucleotide formed during the synthesis of purine nucleotides It can also be formed by the deamination of adenosine monophosphate by AMP deaminase It can be hydrolysed to inosine Inosinic acid NamesIUPAC name 5 Inosinic acidOther names IMP Hypoxanthine ribotideIdentifiersCAS Number 131 99 7 Y3D model JSmol Interactive imageChEBI CHEBI 17202 YChEMBL ChEMBL1233478 NChemSpider 8264 YECHA InfoCard 100 004 588E number E630 flavour enhancer IUPHAR BPS 5124MeSH Inosine monophosphatePubChem CID 8582UNII TAO7US05G5 YCompTox Dashboard EPA DTXSID4044294InChI InChI 1S C10H13N4O8P c15 6 4 1 21 23 18 19 20 22 10 7 6 16 14 3 13 5 8 14 11 2 12 9 5 17 h2 4 6 7 10 15 16H 1H2 H 11 12 17 H2 18 19 20 t4 6 7 10 m1 s1 YKey GRSZFWQUAKGDAV KQYNXXCUSA N YInChI 1 C10H13N4O8P c15 6 4 1 21 23 18 19 20 22 10 7 6 16 14 3 13 5 8 14 11 2 12 9 5 17 h2 4 6 7 10 15 16H 1H2 H 11 12 17 H2 18 19 20 t4 6 7 10 m1 s1Key GRSZFWQUAKGDAV KQYNXXCUBUSMILES O C3 N C Nc1c3ncn1 C H 2O C H C H O C H 2O COP O O OPropertiesChemical formula C 10H 13N 4O 8PMolar mass 348 208 g mol 1Except 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 The enzyme deoxyribonucleoside triphosphate pyrophosphohydrolase encoded by YJR069C in Saccharomyces cerevisiae and containing d ITPase and d XTPase activities hydrolyzes inosine triphosphate ITP releasing pyrophosphate and IMP 1 Important derivatives of inosinic acid include the purine nucleotides found in nucleic acids and adenosine triphosphate which is used to store chemical energy in muscle and other tissues In the food industry inosinic acid and its salts such as disodium inosinate are used as flavor enhancers It is known as E number reference E630 Contents 1 Inosinate synthesis 2 Synthesis of other purine nucleotides 3 Regulation of purine nucleotide biosynthesis 4 Applications 5 See also 6 References 7 Further readingInosinate synthesis editMain article Purine metabolism Biosynthesis The inosinate synthesis is complex beginning with a 5 phosphoribosyl 1 pyrophosphate PRPP Enzymes taking part in IMP synthesis constitute a multienzyme complex in the cell Evidence demonstrates that there are multifunctional enzymes and some of them catalyze non sequential steps in the pathway citation needed nbsp This figure shows the pathway described IMP synthesis Synthesis of other purine nucleotides editWithin a few steps inosinate becomes AMP or GMP 2 Both compounds are RNA nucleotides 2 AMP differs from inosinate by the replacement of IMP s carbon 6 carbonyl with an amino group The interconversion of AMP and IMP occurs as part of the purine nucleotide cycle 3 GMP is formed by the inosinate oxidation to xanthylate XMP and afterwards adds an amino group on carbon 2 Hydrogen acceptor on inosinate oxidation is NAD Finally carbon 2 gains the amino group by spending an ATP molecule which becomes AMP 2Pi While AMP synthesis requires GTP GMP synthesis uses ATP That difference offers an important regulation possibility nbsp Glutamine PRPP amidotransferaseRegulation of purine nucleotide biosynthesis editInosinate and many other molecules inhibit the synthesis of 5 phosphoribosylamine from 5 phosphoribosyl 1 pyrophosphate PRPP disabling the enzyme that catalyzes the reaction glutamine 5 phosphoribosyl 1 pyrophosphate amidotransferase In other words when levels of inosinate are high glutamine 5 phosphoribosyl 1 pyrophosphate amidotransferase is inhibited and as a consequence inosinate levels decrease Also as a result adenylate and guanylate are not produced which means that RNA synthesis cannot be completed because of the lack of these two important RNA nucleotides Applications editInosinic acid can be converted into various salts including disodium inosinate E631 dipotassium inosinate E632 and calcium inosinate E633 These three compounds are used as flavor enhancers for the basic taste umami or savoriness with a comparatively high effectiveness They are mostly used in soups sauces and seasonings for the intensification and balance of the flavor of meat See also editThioinosinic acid Phosphatidyl inositol Glutamate flavoring Kikunae Ikeda Umami Ajinomoto Tien Chu Ve Tsin Glutamic acid Disodium glutamate Monopotassium glutamate Disodium inosinate Guanosine monophosphate Adenosine monophosphateReferences edit Davies O Mendes P Smallbone K Malys N 2012 Characterisation of multiple substrate specific d ITP d XTPase and modelling of deaminated purine nucleotide metabolism BMB Reports 45 4 259 64 doi 10 5483 BMBRep 2012 45 4 259 PMID 22531138 a b Mader M M Henry J R 2007 01 01 Taylor John B Triggle David J eds 7 03 Antimetabolites Comprehensive Medicinal Chemistry II Oxford Elsevier pp 55 79 doi 10 1016 b0 08 045044 x 00204 2 ISBN 978 0 08 045044 5 retrieved 2020 12 17 Voet D Voet J G Biochemistry 3rd Edition John Wiley amp Sons Inc 2004 pg 1095Further reading editBerg Jeremy M Bioquimica Editorial Reverte 6ena edicio Barcelona 2007 Nelson David L Principles of biochemistry Editorial W H Freeman and Company 4th edition New York 2005 Retrieved from https en wikipedia org w index php title Inosinic acid amp oldid 1183360020, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.