Guanosine diphosphate mannose

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.

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
3D model (JSmol)
ChEBI
ChemSpider
MeSH Guanosine+Diphosphate+Mannose
UNII
  • 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 checkY
    Key: MVMSCBBUIHUTGJ-GDJBGNAASA-N checkY
  • 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
  • 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
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).
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Infobox references

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

Biosynthesis

GDP-mannose is produced from GTP and mannose-6-phosphate by the enzyme mannose-1-phosphate guanylyltransferase.[2]

One of the enzymes from the family of nucleootidyl-transferases, GDP-Mannose Pyrophosphorylase (GDP-MP) is an pervasive enzyme found in bacteria, fungi, plants, and animals.[3]

References
  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.
  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. 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.

See also
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