Uridine diphosphate glucose

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Uridine diphosphate glucose

IUPAC name [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] hydrogen phosphate
Other names UDP-glucose
Identifiers
CAS number	133-89-1^Y
PubChem	8629
ChemSpider	8308^Y
MeSH	Uridine+Diphosphate+Glucose
ChEBI	CHEBI:52249^Y
ChEMBL	CHEMBL375951^Y
IUPHAR ligand	1783
Jmol-3D images	{{#if:O=P(O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)(O)OP(=O)(O)OC[C@H]3O[C@@H](N2/C=C\C(=O)NC2=O)[C@H](O)[C@@H]3O\|Image 1
SMILES O=P(O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)(O)OP(=O)(O)OC[C@H]3O[C@@H](N2/C=C\C(=O)NC2=O)[C@H](O)[C@@H]3O
InChI InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1^Y Key: HSCJRCZFDFQWRP-JZMIEXBBSA-N^Y InChI=1/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1 Key: HSCJRCZFDFQWRP-JZMIEXBBBU
Properties
Molecular formula	C₁₅H₂₄N₂O₁₇P₂
Molar mass	566.302 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Uridine diphosphate glucose (uracil-diphosphate glucose, UDP-glucose) is a nucleotide sugar. It is involved in glycosyltransferase reactions in metabolism.

Functions

It is used in nucleotide sugars metabolism as an activated form of glucose as a substrate for enzymes called glucosyltransferases.^[1]

It is a precursor of glycogen and can be converted into UDP-galactose and UDP-glucuronic acid, which can then be used as substrates by the enzymes that make polysaccharides containing galactose and glucuronic acid.

UDP-glucose can also be used as a precursor of sucrose lipopolysaccharides, and glycosphingolipids.

Components

UDP-glucose consists of the pyrophosphate group, the pentose sugar ribose, glucose, and the nucleobase uracil.

References

↑ Rademacher T, Parekh R, Dwek R (1988). "Glycobiology". Annu Rev Biochem 57: 785–838. doi:10.1146/annurev.bi.57.070188.004033. PMID 3052290.

v t e Types of nucleotide sugars

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

Biochemical families: carbohydrates alcohols glycoproteins glycosides lipids eicosanoids fatty acids / intermediates phospholipids sphingolipids steroids nucleic acids constituents / intermediates proteins Amino acids / intermediates tetrapyrroles / intermediates

Fructose and galactose metabolic intermediates

Fructose

Fructose-1-phosphate → DHAP/Glyceraldehyde → Glyceraldehyde 3-phosphate

Galactose

Galactose-1-phosphate → Glucose 1-phosphate → Glucose 6-phosphate → Fructose 6-phosphate

Uridine diphosphate galactose Uridine diphosphate glucose

Galactitol Iditol

Mannose

Mannose-6-phosphate → Fructose 6-phosphate

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m (A16/C10), i (k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

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Uridine diphosphate glucose

Functions

Components

References

See also