Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:32:05 UTC
Update Date2024-04-30 19:37:50 UTC
Metabolite IDMMDBc0029554
Metabolite Identification
Common NameGDP-L-Fucose
DescriptionGDP-L-fucose is a sugar nucleotide and a readily available source of fucose. The monosaccharide plays several important metabolic roles in complex carbohydrates and in glycoproteins. Fucosylated oligosaccharides are involved in cell-cell recognition, selectin-mediated leukocyte-endothelial adhesion, and mouse embryogenesis. Fucose is made available during the synthesis of fucosylated glycolipids, oligosaccharides, and glycoproteins via a sugar nucleotide intermediate, specifically GDP-L-fucose. GTP-L-fucose pyrophosphorylase (GFPP, E. C. 2.7.7.30) catalyzes the reversible condensation of guanosine triphosphate and beta-L-fucose-1-phosphate to form the nucleotide-sugar GDP-L-fucose.
Structure
Synonyms
ValueSource
(6-Deoxy-beta-L-galactopyranosyl) esterHMDB
GDP FucoseHMDB
GDP-beta-L-FucoseHMDB
Guanosine diphosphate fucoseHMDB
Guanosine diphosphofucoseHMDB
Diphosphate fucose, guanosineHMDB
Diphosphofucose, guanosineHMDB
Fucose, GDPHMDB
Fucose, guanosine diphosphateHMDB
GDP-FucoseHMDB
GDP-Β-L-fucoseHMDB
Guanosine 5'-diphosphate L-fucoseHMDB
Guanosine 5'-diphospho-fucoseHMDB
Guanosine 5'-diphosphofucoseHMDB
Guanosine 5’-diphosphate L-fucoseHMDB
Guanosine 5’-diphospho-fucoseHMDB
Guanosine 5’-diphosphofucoseHMDB
GDP-L-fucoseHMDB
Molecular FormulaC16H25N5O15P2
Average Mass589.3417
Monoisotopic Mass589.082238179
IUPAC Name[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid
Traditional Namegdp-L-fucose
CAS Registry Number15839-70-0
SMILES
C[C@@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=C(N)NC3=O)[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C16H25N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,7-11,14-15,22-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5+,7+,8+,9+,10+,11-,14+,15?/m0/s1
InChI KeyLQEBEXMHBLQMDB-QIXZNPMTSA-N