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Record Information
Version	2.0
Creation Date	2012-05-31 13:46:37 -0600
Update Date	2015-06-03 15:53:47 -0600
Secondary Accession Numbers	ECMDB01163
Identification
Name:	Guanosine diphosphate mannose
Description	GDP-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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x993cb7a4> Close
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)phosphoryl)oxy]({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]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.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Purine nucleotides
Sub Class	Purine nucleotide sugars
Direct Parent	Purine nucleotide sugars
Alternative Parents	Purine ribonucleoside diphosphates Purine ribonucleoside monophosphates Pentose phosphates Glycosylamines Monosaccharide phosphates Organic pyrophosphates Purines and purine derivatives Monoalkyl phosphates Hydroxypyrimidines Oxanes N-substituted imidazoles Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Polyols Oxacyclic compounds Azacyclic compounds Organic oxides Hydrocarbon derivatives Organonitrogen compounds Organopnictogen compounds Primary alcohols
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 Framework	Aromatic heteropolycyclic compounds
External Descriptors	GDP-D-mannose (CHEBI:15820 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 7.77 g/L ALOGPS logP -1.8 ALOGPS logP -5.3 ChemAxon logS -1.9 ALOGPS pKa (Strongest Acidic) 1.73 ChemAxon pKa (Strongest Basic) -3.6 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 16 ChemAxon Hydrogen Donor Count 10 ChemAxon Polar Surface Area 327.43 Ų ChemAxon Rotatable Bond Count 9 ChemAxon Refractivity 118.51 m³·mol⁻¹ ChemAxon Polarizability 48.72 ų ChemAxon Number of Rings 4 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
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 II PW000887 Mannose Metabolism PW000822 colanic acid building blocks biosynthesis PW000951
KEGG Pathways:	Amino sugar and nucleotide sugar metabolism ec00520 Ascorbate and aldarate metabolism ec00053 Fructose and mannose metabolism ec00051 Metabolic pathways eco01100
EcoCyc Pathways:	GDP-L-fucose biosynthesis I (from GDP-D-mannose) PWY-66 GDP-mannose biosynthesis PWY-5659
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-05bu-5842490000-d73f755e03b8ad234b29 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-01r6-7882509000-02adbc06a0f79e803d88 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF 32V, positive splash10-0a4i-0000209000-fa2b35ba4f2fbdff74a3 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF 32V, negative splash10-0udi-3401309000-93213e14894fde4ba5c2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Negative splash10-0udi-0001309000-586a7f020650fe518e5f View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Positive splash10-0udi-0900000000-bba5489b865ff8d5ba78 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Positive splash10-0006-0100900000-d5b51af9c9e096503197 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Positive splash10-0udi-0900400000-3410bfae1c82b5e08999 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Negative splash10-00b9-9434300000-661dad8f3e9cd9b10a38 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Negative splash10-0udi-0000009000-c84788b57e1d68c3a299 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0udi-0910510000-30a5518df6f0f53ad7b7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0udi-0910000000-48aef418f3aa94cc35f8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0udi-1900000000-438261daf883fac47d6c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0udi-1901325000-e5d0bcd5db4a59b606f8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0udi-1901100000-a8c00836fd0ca5a71ad1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0pdl-3900000000-358726d071759c859d9e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0udi-0000009000-3f663b5fce4f431e1e25 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0udi-4701986000-bb5e3a66be23d7de55e6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-05i0-3911810000-ee275d8a12bcf1e5065c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0udi-0900002000-37d2f661727ecc1c915a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0udi-0900001000-de8f3c7c7e6a620f0e90 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0udr-2930000000-7a0fc600f843201b86c4 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
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
Links
External Links:	Resource Link CHEBI ID 15820 HMDB ID HMDB01163 Pubchem Compound ID 732 Kegg ID C00096 ChemSpider ID 17372 Wikipedia Guanosine diphosphate mannose BioCyc ID GDP-MANNOSE EcoCyc ID GDP-MANNOSE Ligand Expo GDD

Enzymes