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
InChIKey:
Synonyms
- UDPG
- UDP-glucose
- UDP-D-glucose
- UDPglucose
- Uridine diphosphate glucose
Databases
MetaCyc:
CPD-12575
BiGG:
udpg
KEGG:
C00029
PubChem (CID):
16667346
ChemSpider:
10239191
CAS:
133-89-1
PupChem (SID):
3331
CHEMBL:
CHEMBL375951
PDB-CCD:
UPG
NIKKAJI:
J9.610E
HMDB:
HMDB60079
MetaNetX:
MNXM722710
KNApSAcK:
C00001514