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Guanosine diphosphate mannose

December 15, 2023

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
  • 3123-67-9 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:15820 Y
ChemSpider
  • 17372 Y
MeSH Guanosine+Diphosphate+Mannose
  • 18396
UNII
  • SA0B77H8CS Y
  • 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
  • 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).
Y verify (what is YN ?)

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

Biosynthesis edit

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 edit

  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 edit

 

This biochemistry article is a stub. You can help Wikipedia by expanding it.

December 15, 2023
guanosine, diphosphate, mannose, mannose, nucleotide, sugar, that, substrate, glycosyltransferase, reactions, metabolism, this, compound, substrate, enzymes, called, mannosyltransferases, namesiupac, name, guanosine, mannopyranosyl, dihydrogen, diphosphate, sy. 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 NamesIUPAC name Guanosine 5 a 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 diphosphateIdentifiersCAS Number 3123 67 9 Y3D model JSmol Interactive imageChEBI CHEBI 15820 YChemSpider 17372 YMeSH Guanosine Diphosphate MannosePubChem CID 18396UNII SA0B77H8CS YInChI 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 YKey MVMSCBBUIHUTGJ GDJBGNAASA N YInChI 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 s1Key MVMSCBBUIHUTGJ GDJBGNAABKSMILES 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 4OPropertiesChemical formula C16H25N5O16P2Molar mass 605 341 g molExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Known as donor of activated mannose in all glycolytic reactions GDP mannose is essential in eukaryotes 1 Biosynthesis editGDP 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 edit 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 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 Pomel Sebastien Mao Wei Ha Duong Tap Cave 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 editNucleoside Nucleotide Guanosine Guanosine diphosphate nbsp This biochemistry article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Guanosine diphosphate mannose amp oldid 1152836484, wikipedia, wiki, book, books, library,

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