GDP-mannose

Guanosine diphosphate mannose
Names
	IUPAC name Guanosine 5′-(α-D-mannopyranosyl dihydrogen diphosphate)
	Systematic IUPAC name O1-{[(2R,3S,4R,5R)-5-(2-Amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl} O3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] dihydrogen diphosphate
Identifiers
CAS Number	3123-67-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15820 ;
ChemSpider	17372 ;
MeSH	Guanosine+Diphosphate+Mannose
PubChem CID	18396;
UNII	SA0B77H8CS ;
	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 Key: MVMSCBBUIHUTGJ-GDJBGNAASA-N ; 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;
	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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Guanosine diphosphate mannose

Chemical compound

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.

Quick Facts Names, Identifiers ...

Known as donor of activated mannose in all glycolytic reactions, GDP-mannose is essential in eukaryotes.^[1]

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This article uses material from the Wikipedia article GDP-mannose, and is written by contributors. Text is available under a CC BY-SA 4.0 International License; additional terms may apply. Images, videos and audio are available under their respective licenses.

[1] [1]
Stewart, James; Curtis, Joan; Spurck, Timothy P.; Ilg, Thomas; Garami, Attila; Baldwin, Tracey; Courret, Nathalie; McFadden, Geoffrey I.; Davis, Antony; Handman, Emanuela (July 2005). "Characterisation of a Leishmania mexicana knockout lacking guanosine diphosphate-mannose pyrophosphorylase". International Journal for Parasitology. 35 (8): 861–873. doi:10.1016/j.ijpara.2005.03.008. PMID 15936761.

[Reeves-2] [2]
Samuel G, Reeves P (2003). "Biosynthesis of O-antigens: genes and pathways involved in nucleotide sugar precursor synthesis and O-antigen assembly". Carbohydrate Research. 338 (23): 2503–19. doi:10.1016/j.carres.2003.07.009. PMID 14670712.

[3] [3]
Pomel, Sébastien; Mao, Wei; Ha-Duong, Tâp; Cavé, Christian; Loiseau, Philippe M. (2019-05-31). "GDP-Mannose Pyrophosphorylase: A Biologically Validated Target for Drug Development Against Leishmaniasis". Frontiers in Cellular and Infection Microbiology. 9: 186. doi:10.3389/fcimb.2019.00186. ISSN 2235-2988. PMC 6554559. PMID 31214516.

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GDP-mannose

Guanosine diphosphate mannose

Biosynthesis

References

See also

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Names

IUPAC name Guanosine 5′-(α-D-mannopyranosyl dihydrogen diphosphate)
Systematic IUPAC name O¹-{[(2R,3S,4R,5R)-5-(2-Amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl} O³-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] dihydrogen diphosphate
Identifiers
CAS Number	3123-67-9^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15820^Y
ChemSpider	17372^Y
MeSH	Guanosine+Diphosphate+Mannose
PubChem CID	18396
UNII	SA0B77H8CS^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
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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references