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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:56 UTC
HMDB IDHMDB01163
Secondary Accession NumbersNone
Metabolite Identification
Common NameGuanosine diphosphate mannose
DescriptionGDP-mannose is a nucleoside diphosphate sugar that is important in the production of fucosylated oligosaccharides. In particular, GDP-mannose is converted to GDP-fucose, which is the fucose donor in the construction of all mammalian fucosylated glycans. 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
ValueSource
GDP-D-MannoseChEBI
GDPmannoseChEBI
Guanosine 5'-(trihydrogen diphosphate), mono-alpha-D-mannopyranosyl esterChEBI
Guanosine diphosphate mannoseChEBI
Guanosine diphosphomannoseChEBI
Guanosine pyrophosphate mannoseChEBI
GDP MannoseHMDB
GDP-GlucoseHMDB
GDP-MannoseHMDB
Chemical FormulaC16H25N5O16P2
Average Molecular Weight605.3411
Monoisotopic Molecular Weight605.077152801
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 Nameguanosine diphosphomannose
CAS Registry Number3123-67-9
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
InChI Identifier
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
InChI KeyInChIKey=MVMSCBBUIHUTGJ-GDJBGNAASA-N
Chemical Taxonomy
DescriptionThis compound 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
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Purine
  • Imidazopyrimidine
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.77 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity118.51 m3·mol-1ChemAxon
Polarizability48.77 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Fructose and Mannose DegradationSMP00064map00051
Fructose intolerance, hereditarySMP00725Not Available
FructosuriaSMP00561Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012326
KNApSAcK IDC00007246
Chemspider ID17372
KEGG Compound IDC00096
BioCyc IDGDP-MANNOSE
BiGG ID1460457
Wikipedia LinkGuanosine diphosphate mannose
NuGOwiki LinkHMDB01163
Metagene LinkHMDB01163
METLIN ID6045
PubChem Compound18396
PDB IDGDD
ChEBI ID15820
References
Synthesis ReferenceHuang, 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
General References
  1. Becker DJ, Lowe JB: Fucose: biosynthesis and biological function in mammals. Glycobiology. 2003 Jul;13(7):41R-53R. Epub 2003 Mar 19. [12651883 ]

Enzymes

General function:
Involved in biosynthetic process
Specific function:
Mannosylates Man(2)GlcNAc(2)-dolichol diphosphate and Man(1)GlcNAc(2)-dolichol diphosphate to form Man(3)GlcNAc(2)-dolichol diphosphate.
Gene Name:
ALG2
Uniprot ID:
Q9H553
Molecular weight:
47091.075
Reactions
Guanosine diphosphate mannose + D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol → Guanosine diphosphate + D-Man-alpha-(1->3)-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-GlcNAc-diphosphodolicholdetails
Guanosine diphosphate mannose + D-Man-alpha-(1->3)-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol → Guanosine diphosphate + D-Man-alpha-(1->3)-(D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolicholdetails
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Transfers mannose from GDP-mannose to dolichol monophosphate to form dolichol phosphate mannose (Dol-P-Man) which is the mannosyl donor in pathways leading to N-glycosylation, glycosyl phosphatidylinositol membrane anchoring, and O-mannosylation of proteins.
Gene Name:
DPM1
Uniprot ID:
O60762
Molecular weight:
29633.995
Reactions
Guanosine diphosphate mannose + Dolichol-20 → Guanosine diphosphate + Dolichyl beta-D-mannosyl phosphatedetails
Guanosine diphosphate mannose + Dolichol-20 → Guanosine diphosphate + Dolichyl phosphate D-mannosedetails
General function:
Involved in catalytic activity
Specific function:
Conversion of GDP-D-mannose to GDP-4-keto-6-D-deoxymannose.
Gene Name:
GMDS
Uniprot ID:
O60547
Molecular weight:
39053.295
Reactions
Guanosine diphosphate mannose → GDP-4-Dehydro-6-deoxy-D-mannose + Waterdetails
General function:
Involved in biosynthetic process
Specific function:
Participates in the formation of the lipid-linked precursor oligosaccharide for N-glycosylation. Involved in assembling the dolichol-pyrophosphate-GlcNAc(2)-Man(5) intermediate on the cytoplasmic surface of the ER.
Gene Name:
ALG1
Uniprot ID:
Q9BT22
Molecular weight:
52517.685
Reactions
Guanosine diphosphate mannose + (N-Acetylglucosaminyl)2-diphosphodolichol → Guanosine diphosphate + beta-1,4-D-mannosylchitobiosyldiphosphodolicholdetails
General function:
Involved in transferase activity
Specific function:
Not Available
Gene Name:
GMPPB
Uniprot ID:
Q9Y5P6
Molecular weight:
42649.34
Reactions
Guanosine triphosphate + D-Mannose 1-phosphate → Pyrophosphate + Guanosine diphosphate mannosedetails
General function:
Involved in transferase activity
Specific function:
Not Available
Gene Name:
GMPPA
Uniprot ID:
Q96IJ6
Molecular weight:
46290.785
Reactions
Guanosine triphosphate + D-Mannose 1-phosphate → Pyrophosphate + Guanosine diphosphate mannosedetails
General function:
Not Available
Specific function:
Mannosyltransferase involved in the last steps of the synthesis of Man5GlcNAc(2)-PP-dolichol core oligosaccharide on the cytoplasmic face of the endoplasmic reticulum. Catalyzes the addition of the 4th and 5th mannose residues to the dolichol-linked oligosaccharide chain.
Gene Name:
ALG11
Uniprot ID:
Q2TAA5
Molecular weight:
55650.595
Reactions
Guanosine diphosphate mannose + D-Man-alpha-(1->3)-(D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol → Guanosine diphosphate + D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolicholdetails
General function:
Not Available
Specific function:
Regulates the biosynthesis of dolichol phosphate-mannose. Essential for the ER localization and stable expression of DPM1.
Gene Name:
DPM2
Uniprot ID:
O94777
Molecular weight:
Not Available
Reactions
Guanosine diphosphate mannose + Dolichol-20 → Guanosine diphosphate + Dolichyl phosphate D-mannosedetails
General function:
Not Available
Specific function:
Stabilizer subunit of the dolichol-phosphate-mannose synthase complex.
Gene Name:
DPM3
Uniprot ID:
Q9P2X0
Molecular weight:
Not Available
Reactions
Guanosine diphosphate mannose + Dolichol-20 → Guanosine diphosphate + Dolichyl phosphate D-mannosedetails