Guanosine diphosphate mannose

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Guanosine diphosphate mannose
GDP-mannose.svg
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
PubChem CID
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 Yes check.svgY
    Key: MVMSCBBUIHUTGJ-GDJBGNAASA-N Yes check.svgY
  • 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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 (GDP-mannose pyrophosphorylase, GDP-MP). [2] This enzyme belongs to a family of nucleotidyl-transferases and is a pervasive enzyme found in bacteria, fungi, plants, and animals. [3]

Related Research Articles

<span class="mw-page-title-main">Mannans</span> Polysaccharides formed from mannose

Mannans are polymers containing the sugar mannose as a principal component. They are a type of polysaccharide found in hemicellulose, a major source of biomass found in higher plants such as softwoods. These polymers also typically contain two other sugars, galactose and glucose. They are often branched.

<span class="mw-page-title-main">Guanosine diphosphate</span> Chemical compound

Guanosine diphosphate, abbreviated GDP, is a nucleoside diphosphate. It is an ester of pyrophosphoric acid with the nucleoside guanosine. GDP consists of a pyrophosphate group, a pentose sugar ribose, and the nucleobase guanine.

<span class="mw-page-title-main">Colitose</span> Chemical compound

Colitose is a mannose-derived 3,6-dideoxysugar produced by certain bacteria. It is a constituent of the lipopolysaccharide. It is the enantiomer of abequose.

In enzymology, a GDP-mannose 6-dehydrogenase (EC 1.1.1.132) is an enzyme that catalyzes the chemical reaction

In enzymology, a GDP-mannose 3,5-epimerase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">GDP-mannose 4,6-dehydratase</span>

The enzyme GDP-mannose 4,6-dehydratase (EC 4.2.1.47) catalyzes the chemical reaction

<span class="mw-page-title-main">Nucleotide sugars metabolism</span>

In nucleotide sugar metabolism a group of biochemicals known as nucleotide sugars act as donors for sugar residues in the glycosylation reactions that produce polysaccharides. They are substrates for glycosyltransferases. The nucleotide sugars are also intermediates in nucleotide sugar interconversions that produce some of the activated sugars needed for glycosylation reactions. Since most glycosylation takes place in the endoplasmic reticulum and golgi apparatus, there are a large family of nucleotide sugar transporters that allow nucleotide sugars to move from the cytoplasm, where they are produced, into the organelles where they are consumed.

Nucleotide sugars are the activated forms of monosaccharides. Nucleotide sugars act as glycosyl donors in glycosylation reactions. Those reactions are catalyzed by a group of enzymes called glycosyltransferases.

In enzymology, a dolichyl-phosphate beta-D-mannosyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a fucose-1-phosphate guanylyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a glucose-1-phosphate cytidylyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a glucose-1-phosphate guanylyltransferase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Glucose-1-phosphate thymidylyltransferase</span>

In enzymology, a glucose-1-phosphate thymidylyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a mannose-1-phosphate guanylyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a mannose-1-phosphate guanylyltransferase (GDP) is an enzyme that catalyzes the chemical reaction

In enzymology, a nucleoside-triphosphate-aldose-1-phosphate nucleotidyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a phosphomannan mannosephosphotransferase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">UTP—hexose-1-phosphate uridylyltransferase</span> Class of enzymes

In enzymology, an UTP—hexose-1-phosphate uridylyltransferase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Thymidine diphosphate glucose</span> Chemical compound

Thymidine diphosphate glucose is a nucleotide-linked sugar consisting of deoxythymidine diphosphate linked to glucose. It is the starting compound for the syntheses of many deoxysugars.

<span class="mw-page-title-main">Cytidine diphosphate glucose</span> Chemical compound

Cytidine diphosphate glucose, often abbreviated CDP-glucose, is a nucleotide-linked sugar consisting of cytidine diphosphate and glucose. This nucleotide saccharide participates in the synthesis of deoxy sugars such as paratose and tyvelose.

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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