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Identification
YMDB IDYMDB00202
NameGuanosine diphosphate mannose
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionGuanosine diphosphate mannose, also known as gdpmannose or GDP-alpha-D-mannose, 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. Guanosine diphosphate mannose is a strong basic compound (based on its pKa). Guanosine diphosphate mannose exists in all living species, ranging from bacteria to humans. Within yeast, guanosine diphosphate mannose participates in a number of enzymatic reactions. In particular, (N-acetylglucosaminyl)2-diphosphodolichol and guanosine diphosphate mannose can be converted into mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol through the action of the enzyme chitobiosyldiphosphodolichol beta-mannosyltransferase. In addition, guanosine diphosphate mannose and dolichol phosphate can be converted into dolichyl β-D-mannosyl phosphate; which is catalyzed by the enzyme dolichyl-phosphate mannose synthase. In yeast, guanosine diphosphate mannose is involved in the metabolic pathway called n-glycan biosynthesis pathway.
Structure
Thumb
Synonyms
  • GDP mannose
  • GDP-D-mannose
  • GDP-glucose
  • GDP-mannose
  • Guanosine Diphosphate Mannose
  • Guanosine diphosphomannose
  • Guanosine pyrophosphate mannose
  • GDPmannose
  • Guanosine 5'-(trihydrogen diphosphate), mono-alpha-D-mannopyranosyl ester
  • GDP-alpha-D-Mannose
  • Guanosine 5'-(trihydrogen diphosphate), mono-a-D-mannopyranosyl ester
  • Guanosine 5'-(trihydrogen diphosphate), mono-α-D-mannopyranosyl ester
  • Guanosine 5'-(trihydrogen diphosphoric acid), mono-a-D-mannopyranosyl ester
  • Guanosine 5'-(trihydrogen diphosphoric acid), mono-alpha-D-mannopyranosyl ester
  • Guanosine 5'-(trihydrogen diphosphoric acid), mono-α-D-mannopyranosyl ester
  • Guanosine pyrophosphoric acid mannose
  • GDP-a-D-Mannose
  • GDP-Α-D-mannose
  • Guanosine diphosphoric acid mannose
  • Pyrophosphate mannose, guanosine
  • Diphosphomannose, guanosine
  • Mannose, guanosine diphosphate
  • Diphosphate mannose, guanosine
  • Mannose, guanosine pyrophosphate
  • Mannose, GDP
  • Guanosine 5'-(trihydrogen diphosphate) P'-mannosyl ester
  • Guanosine 5'-(trihydrogen pyrophosphate) mono-D-mannosyl ester
  • Guanosine 5'-(trihydrogen pyrophosphate) monomannopyranosyl ester
  • Guanosine 5'-(trihydrogen pyrophosphate) monomannosyl ester
  • Guanosine 5'-diphosphate D-mannose
  • Guanosine 5'-pyrophosphate D-mannosyl ester
  • Guanosine 5'-pyrophosphate alpha-D-mannosyl ester
  • Guanosine 5'-pyrophosphate α-D-mannosyl ester
  • Guanosine 5’-(trihydrogen diphosphate) P’-mannosyl ester
  • Guanosine 5’-(trihydrogen pyrophosphate) mono-D-mannosyl ester
  • Guanosine 5’-(trihydrogen pyrophosphate) monomannopyranosyl ester
  • Guanosine 5’-(trihydrogen pyrophosphate) monomannosyl ester
  • Guanosine 5’-diphosphate D-mannose
  • Guanosine 5’-pyrophosphate D-mannosyl ester
  • Guanosine 5’-pyrophosphate α-D-mannosyl ester
CAS number3123-67-9
WeightAverage: 605.3411
Monoisotopic: 605.077152801
InChI KeyMVMSCBBUIHUTGJ-GDJBGNAASA-N
InChIInChI=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
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 Nameguanosine diphosphomannose
Chemical FormulaC16H25N5O16P2
SMILES[H]OC([H])([H])[C@@]1([H])O[C@]([H])(OP(=O)(O[H])OP(=O)(O[H])OC([H])([H])[C@@]2([H])O[C@@]([H])(N3C([H])=NC4=C3N=C(N([H])[H])N([H])C4=O)[C@]([H])(O[H])[C@]2([H])O[H])[C@@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]
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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
  • Golgi
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Amino sugar and nucleotide sugar metabolismPW002413 ThumbThumb?image type=greyscaleThumb?image type=simple
Mannose MetabolismPW002391 ThumbThumb?image type=greyscaleThumb?image type=simple
N-Glycan biosynthesisPW002501 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Amino sugar and nucleotide sugar metabolismec00520 Map00520
Fructose and mannose metabolismec00051 Map00051
N-Glycan biosynthesisec00510 Map00510
SMPDB Reactions
D-Mannose 1-phosphate + GTP + hydronPyrophosphate + Guanosine diphosphate mannose
(N-Acetylglucosaminyl)2-diphosphodolichol + Guanosine diphosphate mannoseMannosyl-(N-acetylglucosaminyl)2-diphosphodolichol + Guanosine diphosphate + hydron
Mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol + Guanosine diphosphate mannose(Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol + Guanosine diphosphate + hydron
(Mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol + Guanosine diphosphate mannoseGuanosine diphosphate + hydron + (Mannosyl)3-(N-acetylglucosaminyl)2-diphosphodolichol
(Mannosyl)3-(N-acetylglucosaminyl)2-diphosphodolichol + Guanosine diphosphate mannose(Mannosyl)5-(N-acetylglucosaminyl)2-diphosphodolichol + Guanosine diphosphate + hydron
KEGG Reactions
Beta-1,4-D-Mannosylchitobiosyldiphosphodolichol + Guanosine diphosphate mannosealpha-D-mannosyl-beta-D-mannosyldiacetylchitobiosyldiphosphodolichol + hydron + Guanosine diphosphate
Guanosine diphosphate mannose + N,N'-diacetylchitobiosyldiphosphodolicholBeta-1,4-D-Mannosylchitobiosyldiphosphodolichol
dolichyl phosphate + Guanosine diphosphate mannoseGuanosine diphosphate + dolichyl D-mannosyl phosphate
GTP + hydron + D-Mannose 1-phosphatePyrophosphate + Guanosine diphosphate mannose
inositol-P-ceramide C (C26) + Guanosine diphosphate mannose ↔ mannosylinositol phosphorylceramide
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Romero, P. A., Lussier, M., Sdicu, A. M., Bussey, H., Herscovics, A. (1997). "Ktr1p is an alpha-1,2-mannosyltransferase of Saccharomyces cerevisiae. Comparison of the enzymic properties of soluble recombinant Ktr1p and Kre2p/Mnt1p produced in Pichia pastoris." Biochem J 321 ( Pt 2):289-295.9020857
  • Huh, W. K., Falvo, J. V., Gerke, L. C., Carroll, A. S., Howson, R. W., Weissman, J. S., O'Shea, E. K. (2003). "Global analysis of protein localization in budding yeast." Nature 425:686-691.14562095
  • Lobsanov, Y. D., Romero, P. A., Sleno, B., Yu, B., Yip, P., Herscovics, A., Howell, P. L. (2004). "Structure of Kre2p/Mnt1p: a yeast alpha1,2-mannosyltransferase involved in mannoprotein biosynthesis." J Biol Chem 279:17921-17931.14752117
  • Funato, K., Vallee, B., Riezman, H. (2002). "Biosynthesis and trafficking of sphingolipids in the yeast Saccharomyces cerevisiae." Biochemistry 41:15105-15114.12484746
  • Lussier, M., Sdicu, A. M., Camirand, A., Bussey, H. (1996). "Functional characterization of the YUR1, KTR1, and KTR2 genes as members of the yeast KRE2/MNT1 mannosyltransferase gene family." J Biol Chem 271:11001-11008.8631921
  • Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834
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.
External Links:
ResourceLink
CHEBI ID15820
HMDB IDHMDB01163
Pubchem Compound ID732
Kegg IDC00096
ChemSpider ID24608058
FOODB IDFDB012326
WikipediaGuanosine diphosphate mannose
BioCyc IDGDP-MANNOSE

Enzymes

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:
P14020
Molecular weight:
30362.0
Reactions
GDP-mannose + dolichyl phosphate → GDP + dolichyl D-mannosyl phosphate.
General function:
Involved in enzyme regulator activity
Specific function:
Required for calcium regulation. May regulate calcium accumulation by a non-vacuole organelle. Also regulates the activity of CSH1 and SUR1 during mannosyl phosphorylinositol ceramide synthesis
Gene Name:
CSG2
Uniprot ID:
P35206
Molecular weight:
45441.60156
Reactions
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:
P16661
Molecular weight:
51928.5
Reactions
GDP-mannose + chitobiosyldiphosphodolichol → GDP + beta-1,4-D-mannosylchitobiosyldiphosphodolichol.
General function:
Involved in mannosyltransferase activity
Specific function:
Required for the attachment of the third mannose residue of O-linked saccharides
Gene Name:
KRE2
Uniprot ID:
P27809
Molecular weight:
51386.19922
Reactions
General function:
Involved in mannosyltransferase activity
Specific function:
Mannosyltransferase that transfers a mannose residue from GDP-mannose to a range of acceptors in vitro
Gene Name:
KTR1
Uniprot ID:
P27810
Molecular weight:
46021.69922
Reactions
General function:
Involved in mannosyltransferase activity
Specific function:
Involved in N-linked glycosylation
Gene Name:
KTR2
Uniprot ID:
P33550
Molecular weight:
50650.89844
Reactions
General function:
Involved in mannosyltransferase activity
Specific function:
Possible glycosyltransferase
Gene Name:
KTR3
Uniprot ID:
P38130
Molecular weight:
47482.0
Reactions
General function:
Involved in mannosyltransferase activity
Specific function:
Possible glycosyltransferase involved in N-linked glycosylation
Gene Name:
YUR1
Uniprot ID:
P26725
Molecular weight:
50835.60156
Reactions
General function:
Involved in transferase activity
Specific function:
Involved in cell wall synthesis where it is required for glycosylation. Involved in cell cycle progression through cell- size checkpoint
Gene Name:
MPG1
Uniprot ID:
P41940
Molecular weight:
39565.60156
Reactions
GTP + alpha-D-mannose 1-phosphate → diphosphate + GDP-mannose.
General function:
Cell wall/membrane/envelope biogenesis
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:
P43636
Molecular weight:
58046.5
Reactions
General function:
protein glycosylation
Specific function:
Required for N-linked oligosaccharide assembly. Has a role in the last step of the synthesis of the Man(5)GlcNAc(2)-PP-dolichol core oligosaccharide on the cytoplasmic face of the endoplasmic reticulum.
Gene Name:
ALG11
Uniprot ID:
P53954
Molecular weight:
63142.705
Reactions

Transporters

General function:
Involved in transmembrane transport
Specific function:
Involved in the import of GDP-mannose from the cytoplasm into the Golgi lumen. Defective copy causes severe glycosylation defect and abnormal retention of soluble endoplasmic reticulum proteins. Involved in vanadate sensitivity
Gene Name:
VRG4
Uniprot ID:
P40107
Molecular weight:
37018.30078