Record Information
Version2.0
Creation Date2012-05-31 13:46:37 -0600
Update Date2015-06-03 15:53:47 -0600
Secondary Accession Numbers
  • ECMDB01163
Identification
Name:Guanosine diphosphate mannose
DescriptionGDP-mannose is a nucleoside diphosphate sugar that is important in the production of fucosylated oligosaccharides. GDP-mannose is transformed to GDP-fucose via three enzymatic reactions carried out by two proteins, GDP-mannose 4,6-dehydratase (GMD) and a second enzyme, GDP-keto-6-deoxymannose 3,5-epimerase, 4-reductase. GDP-mannose 4,6-dehydratase (EC 4.2.1.47) catalyzes the chemical reaction: GDP-mannose <--> GDP-4-dehydro-6-deoxy-D-mannose + H2O. The epimerase converts the GDP-4-dehydro-6-deoxy-D-mannose to GDP-fucose. (PMID: 12651883). GDP-mannose is also synthesized from mannose 1-phosphate via the enzyme ATP-mannose-1-phosphate-guanyltransferase and GTP.
Structure
Thumb
Synonyms:
  • GDP Mannose
  • GDP-D-Mannose
  • GDP-Glucose
  • GDP-Man
  • GDP-Mannose
  • GDP-α-D-mannose
  • Guanosine Diphosphate Mannose
  • Guanosine diphosphomannose
  • Guanosine diphosphoric acid mannose
  • Guanosine pyrophosphate mannose
  • Guanosine pyrophosphoric acid mannose
Chemical Formula:C16H25N5O16P2
Weight:Average: 605.3411
Monoisotopic: 605.077152801
InChI Key:MVMSCBBUIHUTGJ-GDJBGNAASA-N
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
CAS number:3123-67-9
IUPAC Name:{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid
Traditional IUPAC Name:guanosine diphosphomannose
SMILES:NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C(=O)N1
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine nucleotide sugars
Direct ParentPurine nucleotide sugars
Alternative Parents
Substituents
  • Purine nucleotide sugar
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organic oxygen compound
  • Alcohol
  • Organic oxide
  • Primary alcohol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility7.77 g/LALOGPS
logP-1.8ALOGPS
logP-5.5ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.31ChemAxon
pKa (Strongest Basic)3.19ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area327.43 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity118.51 m³·mol⁻¹ChemAxon
Polarizability48.77 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Guanosine diphosphate + Hydrogen ion + D-Mannose 1-phosphate > Guanosine diphosphate mannose + Phosphate
Guanosine diphosphate mannose + Water > Guanosine diphosphate + Hydrogen ion + D-Mannose
Guanosine diphosphate mannose <> GDP-4-Dehydro-6-deoxy-D-mannose + Water
Guanosine diphosphate mannose + Water > Guanosine monophosphate +2 Hydrogen ion + D-Mannose 1-phosphate
Guanosine triphosphate + D-Mannose 1-phosphate <> Pyrophosphate + Guanosine diphosphate mannose
Guanosine diphosphate mannose + Water > Hydrogen ion + Guanosine monophosphate + D-Mannose 1-phosphate
Hydrogen ion + D-Mannose 1-phosphate + Guanosine triphosphate > Guanosine diphosphate mannose + Pyrophosphate
Guanosine diphosphate mannose > Water + GDP-4-Dehydro-6-deoxy-D-mannose
Guanosine diphosphate mannose + Water > Guanosine diphosphate + D-Mannose
Guanosine triphosphate + Alpha-D-mannose 1-phosphate > Pyrophosphate + Guanosine diphosphate mannose
Guanosine diphosphate mannose + Water > Guanosine monophosphate + Alpha-D-mannose 1-phosphate
D-Mannose 1-phosphate + Guanosine triphosphate + Hydrogen ion > Pyrophosphate + Guanosine diphosphate mannose
α-D-mannose 1-phosphate + Guanosine triphosphate + Hydrogen ion > Guanosine diphosphate mannose + Pyrophosphate
Guanosine diphosphate mannose > Water + GDP-4-dehydro-6-deoxy-α-D-mannose
Guanosine diphosphate mannose > GDP-4-Dehydro-6-L-deoxygalactose + GDP-4-Dehydro-6-L-deoxygalactose
Guanosine triphosphate + D-Mannose 1-phosphate <> Pyrophosphate + Guanosine diphosphate mannose
Guanosine diphosphate mannose <> GDP-4-Dehydro-6-deoxy-D-mannose + Water
Guanosine triphosphate + D-Mannose 1-phosphate <> Pyrophosphate + Guanosine diphosphate mannose
Guanosine diphosphate mannose <> GDP-4-Dehydro-6-deoxy-D-mannose + Water
SMPDB Pathways:
Amino sugar and nucleotide sugar metabolism IIPW000887 ThumbThumb?image type=greyscaleThumb?image type=simple
Mannose MetabolismPW000822 ThumbThumb?image type=greyscaleThumb?image type=simple
colanic acid building blocks biosynthesisPW000951 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • GDP-L-fucose biosynthesis I (from GDP-D-mannose) PWY-66
  • GDP-mannose biosynthesis PWY-5659
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05bu-5842490000-d73f755e03b8ad234b29View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01r6-7882509000-02adbc06a0f79e803d88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0910510000-30a5518df6f0f53ad7b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0910000000-48aef418f3aa94cc35f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1900000000-438261daf883fac47d6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1901325000-e5d0bcd5db4a59b606f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1901100000-a8c00836fd0ca5a71ad1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pdl-3900000000-358726d071759c859d9eView in MoNA
References
References:
  • Becker, D. J., Lowe, J. B. (2003). "Fucose: biosynthesis and biological function in mammals." Glycobiology 13:41R-53R. Pubmed: 12651883
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Huang, Gang-Liang; Liu, Xiang; Zhang, Hou-Cheng; Wang, Peng-George. A facile two-step chemo-enzymatic synthesis of GDP-mannose. Letters in Organic Chemistry (2006), 3(9), 668-669.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15820
HMDB IDHMDB01163
Pubchem Compound ID732
Kegg IDC00096
ChemSpider ID17372
WikipediaGuanosine diphosphate mannose
BioCyc IDGDP-MANNOSE
EcoCyc IDGDP-MANNOSE
Ligand ExpoGDD

Enzymes

General function:
Involved in catalytic activity
Specific function:
GDP-mannose = GDP-4-dehydro-6-deoxy-D-mannose + H(2)O
Gene Name:
gmd
Uniprot ID:
P0AC88
Molecular weight:
42047
Reactions
GDP-mannose = GDP-4-dehydro-6-deoxy-D-mannose + H(2)O.
General function:
Involved in nucleotidyltransferase activity
Specific function:
Involved in the biosynthesis of the capsular polysaccharide colanic acid
Gene Name:
manC
Uniprot ID:
P24174
Molecular weight:
53016
Reactions
GTP + alpha-D-mannose 1-phosphate = diphosphate + GDP-mannose.
General function:
Involved in hydrolase activity, acting on acid anhydrides, in phosphorus-containing anhydrides
Specific function:
Could participate in the regulation of cell wall biosynthesis by influencing the concentration of GDP-mannose or GDP-glucose in the cell. May be involved in the degradation of GDP-mannose and GDP-glucose, diverting the GDP to the synthesis of GDP-fucose as required. Might also be involved in the biosynthesis of the slime polysaccharide colanic acid
Gene Name:
nudD
Uniprot ID:
P32056
Molecular weight:
18273
Reactions
GDP-D-mannose + H(2)O = GDP + D-mannose.
General function:
Involved in hydrolase activity, acting on acid anhydrides, in phosphorus-containing anhydrides
Specific function:
Catalyzes the hydrolysis of GDP-mannose. Can also use other substrates, catalyzing the hydrolysis of the pyrophosphate bond, releasing a nucleoside monophosphate and a phosphorylated moiety, depending on the substrate
Gene Name:
nudK
Uniprot ID:
P37128
Molecular weight:
21749
Reactions
GDP-mannose + H(2)O = GMP + mannose-1-phosphate.