Guanosine diphosphate mannose

Guanosine diphosphate mannose
Names

IUPAC name [(2R,3S,4R,5R)-5-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl dihydrogen diphosphate
Identifiers
CAS Registry Number	3123-67-9
ChEBI	CHEBI:15820^Y
ChemSpider	17372^Y
InChI InChI=1S/C16H25N5O16P2/c17-16-19-12-6(13(28)20-16)18-3-21(12)14-10(26)8(24)5(34-14)2-33-38(29,30)37-39(31,32)36-15-11(27)9(25)7(23)4(1-22)35-15/h3-5,7-11,14-15,22-27H,1-2H2,(H,29,30)(H,31,32)(H3,17,19,20,28)/t4-,5-,7-,8-,9+,10-,11+,14-,15-/m1/s1^Y Key: MVMSCBBUIHUTGJ-GDJBGNAASA-N^Y InChI=1/C16H25N5O16P2/c17-16-19-12-6(13(28)20-16)18-3-21(12)14-10(26)8(24)5(34-14)2-33-38(29,30)37-39(31,32)36-15-11(27)9(25)7(23)4(1-22)35-15/h3-5,7-11,14-15,22-27H,1-2H2,(H,29,30)(H,31,32)(H3,17,19,20,28)/t4-,5-,7-,8-,9+,10-,11+,14-,15-/m1/s1 Key: MVMSCBBUIHUTGJ-GDJBGNAABK
Jmol-3D images	Image
MeSH	Guanosine+Diphosphate+Mannose
PubChem	18396
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]4O[C@@H](n2c3NC(=N/C(=O)c3nc2)\N)[C@H](O)[C@@H]4O
Properties
Chemical formula	C₁₆H₂₅N₅O₁₆P₂
Molar mass	605.341 g/mol
	Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Y verify (what is: Y/N?)
Infobox references

Guanosine diphosphate mannose or GDP-mannose is a nucleotide sugar that is a substrate for glycosyltransferase reactions in metabolism. This compound is a substrate for enzymes called mannosyltransferases.

Biosynthesis

GDP-mannose is produced from GTP and mannose-6-phosphate by the enzyme mannose-1-phosphate guanylyltransferase.^[1]

↑ Samuel G, Reeves P (2003). "Biosynthesis of O-antigens: genes and pathways involved in nucleotide sugar precursor synthesis and O-antigen assembly". Carbohydr. Res. 338 (23): 2503–19. doi:10.1016/j.carres.2003.07.009. PMID 14670712.