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Uridine diphosphate glucose

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Uridine diphosphate glucose
Names
IUPAC name methoxy-hydroxyphosphoryl] hydrogen phosphate
Other names UDP-glucose
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.657 Edit this at Wikidata
IUPHAR/BPS
MeSH Uridine+Diphosphate+Glucose
PubChem CID
CompTox Dashboard (EPA)
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/s1Key: HSCJRCZFDFQWRP-JZMIEXBBSA-N
  • 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/s1Key: HSCJRCZFDFQWRP-JZMIEXBBBU
SMILES
  • O=P(O1O((O)(O)1O)CO)(O)OP(=O)(O)OC3O(N2/C=C\C(=O)NC2=O)(O)3O
Properties
Chemical formula C15H24N2O17P2
Molar mass 566.302 g/mol
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

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.

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

  1. Rademacher T, Parekh R, Dwek R (1988). "Glycobiology". Annu Rev Biochem. 57: 785–838. doi:10.1146/annurev.bi.57.070188.004033. PMID 3052290.{{cite journal}}: CS1 maint: multiple names: authors list (link)

See also

Types of nucleotide sugars
Fructose and galactose metabolic intermediates
Fructose
Galactose
Mannose
Categories: