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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:48:15 UTC
HMDB IDHMDB0001163
Secondary Accession Numbers
  • HMDB0062759
  • HMDB01163
  • HMDB62759
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
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)phosphoryl)oxy]({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]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 KeyMVMSCBBUIHUTGJ-GDJBGNAASA-N
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
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg207.34730932474
[M-H]-Not Available209.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00000117
[M+H]+Not Available227.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00000117
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030881
KNApSAcK IDC00007246
Chemspider ID17372
KEGG Compound IDC00096
BioCyc IDGDP-MANNOSE
BiGG ID1460457
Wikipedia LinkGuanosine diphosphate mannose
METLIN ID6045
PubChem Compound18396
PDB IDNot Available
ChEBI ID15820
Food Biomarker OntologyNot Available
VMH IDGDPMANN
MarkerDB IDNot Available
Good Scents IDNot Available
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. [PubMed: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