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Uridine diphosphate glucuronic acid

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Uridine diphosphate glucuronic acid
Names
IUPAC name 3--1,3-dihydroxy-1,3-dioxo-1λ,3λ-diphosphoxan-1-yl α-D-glucopyranosiduronic acid
Systematic IUPAC name (2S,3S,4S,5R,6R)-6-methoxy}-1,3-dihydroxy-1,3-dioxo-1λ,3λ-diphosphoxan-1-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
IUPHAR/BPS
MeSH UDP+glucuronic+acid
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: GIFKDHYZEJQSDD-BZYIUNRFSA-J
  • 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/s1Key: GIFKDHYZEJQSDD-DNQFPBLIBB
SMILES
  • O1(O)(O(1O)C(O)=O)O(O)(=O)O(O)(=O)OC2O((O)2O)3C=C(=O)3=O
Properties
Chemical formula C15H22N2O18P2
Molar mass 580.285
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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.

See also

References

  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.
Types of nucleotide sugars


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