UDP-α-D-glucose





Description


UDP-α-D-glucose, or uridine diphosphate glucose, is a nucleotide sugar that plays a critical role in many biochemical processes in living organisms. It is made up of a uracil nucleotide, a ribose sugar, and a diphosphate group, with a glucose molecule attached to the 1' carbon of the ribose sugar. UDP-glucose is involved in the biosynthesis of glycogen, which is a storage form of glucose in animals, and starch, which is the storage form of glucose in plants. UDP-glucose is also used in the production of various glycosylated compounds, such as glycolipids, glycoproteins, and polysaccharides. In addition to its role in biosynthesis, UDP-glucose is also involved in the regulation of certain metabolic pathways. For example, it is a substrate for the synthesis of the signaling molecule cyclic AMP (cAMP) and can also regulate the activity of certain enzymes through allosteric regulation. UDP-glucose is synthesized in cells through the action of the enzyme UDP-glucose pyrophosphorylase, which catalyzes the conversion of glucose-1-phosphate and UTP (uridine triphosphate) to UDP-glucose and pyrophosphate. The reverse reaction is catalyzed by the enzyme UDP-glucose pyrophosphatase.


Chemical Formula:
C15H22N2O17P2
Molecular Weight:
564.289 Daltons
Monoisotopic Mass:
566.0550203765 Daltons
SMILES:
C(O)C1(C(O)C(O)C(O)C(O1)OP(OP(=O)([O-])OCC2(OC(C(O)C(O)2)N3(C=CC(=O)NC(=O)3)))([O-])=O)
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)/p-2/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1

Synonyms
  • UDPG
  • UDP-glucose
  • UDP-D-glucose
  • UDPglucose
  • Uridine diphosphate glucose

Databases
MetaCyc:  CPD-12575
BiGG:  udpg
KEGG:  C00029
PubChem (CID):  16667346
ChemSpider:  10239191
ChEBI:  58885 18066 46229
CAS:  133-89-1
PupChem (SID):  3331
CHEMBL:  CHEMBL375951
PDB-CCD:  UPG
NIKKAJI:  J9.610E
HMDB:  HMDB60079
MetaNetX:  MNXM722710
KNApSAcK:  C00001514