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Uridine diphosphate glucuronic acid

April 16, 2024

UDP-glucuronic acid is a sugar used in the creation of polysaccharides and is an intermediate in the biosynthesis of ascorbic acid (except in primates and guinea pigs). It also participates in the heme degradation process of human.

Uridine diphosphate glucuronic acid
Names
IUPAC name
3-[(5′-Deoxyuridin-5′-yl)oxy]-1,3-dihydroxy-1,3-dioxo-1λ5,3λ5-diphosphoxan-1-yl α-D-glucopyranosiduronic acid
Systematic IUPAC name
(2S,3S,4S,5R,6R)-6-[(3-{[(2R,3S,4R,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}-1,3-dihydroxy-1,3-dioxo-1λ5,3λ5-diphosphoxan-1-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Identifiers
  • 2616-64-0 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17200 N
ChemSpider
  • 19951236 Y
  • 1784
MeSH UDP+glucuronic+acid
  • 17473
UNII
  • 04SZC4MEFQ Y
  • DTXSID00903961
  • InChI=1S/C9H12N2O6.C6H12O13P2/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16;7-1-2(18-20(12,13)14)5(19-21(15,16)17)3(8)4(9)6(10)11/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16);1-5,8-9H,(H,10,11)(H2,12,13,14)(H2,15,16,17)/p-4/t4-,6-,7-,8-;2-,3+,4-,5+/m10/s1 Y
    Key: GIFKDHYZEJQSDD-BZYIUNRFSA-J Y
  • InChI=1/C9H12N2O6.C6H12O13P2/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16;7-1-2(18-20(12,13)14)5(19-21(15,16)17)3(8)4(9)6(10)11/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16);1-5,8-9H,(H,10,11)(H2,12,13,14)(H2,15,16,17)/p-4/t4-,6-,7-,8-;2-,3+,4-,5+/m10/s1
    Key: GIFKDHYZEJQSDD-DNQFPBLIBB
  • O[C@@H]1[C@@H](O)[C@H](O[C@@H]([C@H]1O)C(O)=O)O[P](O)(=O)O[P](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)[N]3C=C[C](=O)[NH][C]3=O
Properties
C15H22N2O18P2
Molar mass 580.285
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 ?)

It is made from UDP-glucose by UDP-glucose 6-dehydrogenase (EC 1.1.1.22) using NAD+ as a cofactor. It is the source of the glucuronosyl group in glucuronosyltransferase reactions.[1][2]

See also edit

References edit

  1. ^ Bontemps Y, Vuillermoz B, Antonicelli F, Perreau C, Danan JL, Maquart FX, Wegrowski Y (Jun 2003). "Specific protein-1 is a universal regulator of UDP-glucose dehydrogenase expression: its positive involvement in transforming growth factor-beta signaling and inhibition in hypoxia". The Journal of Biological Chemistry. 278 (24): 21566–75. doi:10.1074/jbc.M209366200. PMID 12682078.
  2. ^ Sommer BJ, Barycki JJ, Simpson MA (May 2004). "Characterization of human UDP-glucose dehydrogenase. CYS-276 is required for the second of two successive oxidations". The Journal of Biological Chemistry. 279 (22): 23590–6. doi:10.1074/jbc.M401928200. PMID 15044486.


 

This biochemistry article is a stub. You can help Wikipedia by expanding it.

April 16, 2024
uridine, diphosphate, glucuronic, acid, glucuronic, acid, sugar, used, creation, polysaccharides, intermediate, biosynthesis, ascorbic, acid, except, primates, guinea, pigs, also, participates, heme, degradation, process, human, namesiupac, name, deoxyuridin, . UDP glucuronic acid is a sugar used in the creation of polysaccharides and is an intermediate in the biosynthesis of ascorbic acid except in primates and guinea pigs It also participates in the heme degradation process of human Uridine diphosphate glucuronic acid NamesIUPAC name 3 5 Deoxyuridin 5 yl oxy 1 3 dihydroxy 1 3 dioxo 1l5 3l5 diphosphoxan 1 yl a D glucopyranosiduronic acidSystematic IUPAC name 2S 3S 4S 5R 6R 6 3 2R 3S 4R 5R 5 2 4 Dioxo 3 4 dihydropyrimidin 1 2H yl 3 4 dihydroxyoxolan 2 yl methoxy 1 3 dihydroxy 1 3 dioxo 1l5 3l5 diphosphoxan 1 yl oxy 3 4 5 trihydroxyoxane 2 carboxylic acidIdentifiersCAS Number 2616 64 0 Y3D model JSmol Interactive imageChEBI CHEBI 17200 NChemSpider 19951236 YIUPHAR BPS 1784MeSH UDP glucuronic acidPubChem CID 17473UNII 04SZC4MEFQ YCompTox Dashboard EPA DTXSID00903961InChI InChI 1S C9H12N2O6 C6H12O13P2 c12 3 4 6 14 7 15 8 17 4 11 2 1 5 13 10 9 11 16 7 1 2 18 20 12 13 14 5 19 21 15 16 17 3 8 4 9 6 10 11 h1 2 4 6 8 12 14 15H 3H2 H 10 13 16 1 5 8 9H H 10 11 H2 12 13 14 H2 15 16 17 p 4 t4 6 7 8 2 3 4 5 m10 s1 YKey GIFKDHYZEJQSDD BZYIUNRFSA J YInChI 1 C9H12N2O6 C6H12O13P2 c12 3 4 6 14 7 15 8 17 4 11 2 1 5 13 10 9 11 16 7 1 2 18 20 12 13 14 5 19 21 15 16 17 3 8 4 9 6 10 11 h1 2 4 6 8 12 14 15H 3H2 H 10 13 16 1 5 8 9H H 10 11 H2 12 13 14 H2 15 16 17 p 4 t4 6 7 8 2 3 4 5 m10 s1Key GIFKDHYZEJQSDD DNQFPBLIBBSMILES O C H 1 C H O C H O C H C H 1O C O O O P O O O P O O OC C H 2O C H C H O C H 2O N 3C C C O NH C 3 OPropertiesChemical formula C15H22N2O18P2Molar mass 580 285Except 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 It is made from UDP glucose by UDP glucose 6 dehydrogenase EC 1 1 1 22 using NAD as a cofactor It is the source of the glucuronosyl group in glucuronosyltransferase reactions 1 2 See also editGlucuronic acid UDPReferences edit Bontemps Y Vuillermoz B Antonicelli F Perreau C Danan JL Maquart FX Wegrowski Y Jun 2003 Specific protein 1 is a universal regulator of UDP glucose dehydrogenase expression its positive involvement in transforming growth factor beta signaling and inhibition in hypoxia The Journal of Biological Chemistry 278 24 21566 75 doi 10 1074 jbc M209366200 PMID 12682078 Sommer BJ Barycki JJ Simpson MA May 2004 Characterization of human UDP glucose dehydrogenase CYS 276 is required for the second of two successive oxidations The Journal of Biological Chemistry 279 22 23590 6 doi 10 1074 jbc M401928200 PMID 15044486 nbsp This biochemistry article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Uridine diphosphate glucuronic acid amp oldid 1173997256, wikipedia, wiki, book, books, library,

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