Uridine diphosphate glucuronic acid

Uridine diphosphate glucuronic acid
Identifiers

CAS Number	2616-64-0^N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17200^N
ChemSpider	19951236^Y
IUPHAR/BPS	1784
MeSH	UDP+glucuronic+acid
PubChem	17473
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/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
SMILES OC(=O)[C@@H](O)[C@@H](O)[C@H](OP([O-])([O-])=O)[C@H](C=O)OP([O-])([O-])=O.O=C\1NC(=O)N(/C=C/1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O
Properties
Chemical formula	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 ?)
Infobox references

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 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]

References

↑ 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.

Types of nucleotide sugars

CDP-glucose GDP-mannose TDP-glucose UDP-glucose UDP-galactose UDP-glucuronic acid UDP-N-acetylglucosamine

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