uridine diphosphate glucose

{{chembox

| verifiedrevid = 470620377

| ImageFile = UDP-Glucose.svg

| ImageSize =

| IUPACName = Uridine 5′-(α-D-glucopyranosyl dihydrogen diphosphate)

| SystematicName = O1-{[(2R,3S,4R,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxyoxolan-2-yl]methyl} O3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] dihydrogen diphosphate

| OtherNames = UDP-glucose

| Section1 = {{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 8308

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 375951

| 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

| InChIKey = HSCJRCZFDFQWRP-JZMIEXBBBU

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = HSCJRCZFDFQWRP-JZMIEXBBSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 133-89-1

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = V50K1D7P4Y

| PubChem = 8629

| IUPHAR_ligand = 1783

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 52249

| 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

| MeSHName = Uridine+Diphosphate+Glucose

}}

| Section2 = {{Chembox Properties

| Formula = C15H24N2O17P2

| MolarMass = 566.302 g/mol

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

}}

| Section3 = {{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

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

Functions

UDP-glucose is used in nucleotide sugar metabolism as an activated form of glucose, a substrate for enzymes called glucosyltransferases.{{cite journal |vauthors=Rademacher T, Parekh R, Dwek R |title=Glycobiology |journal=Annu Rev Biochem |volume=57 |pages=785–838 |year=1988 |pmid=3052290 |doi=10.1146/annurev.bi.57.070188.004033}}

UDP-glucose 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, ribose, glucose, and uracil.

See also

References

{{reflist}}

{{Nucleotide sugars}}

{{Fructose and galactose metabolic intermediates}}

{{Purinergics}}

Category:Nucleotides

Category:Coenzymes