2.0 2012-05-31 13:52:38 -0600 2015-06-03 15:54:07 -0600 ECMDB01436 M2MDB000386 D-Mannose 1-phosphate D-Mannose 1-phosphate is a normal metabolite intermediate in the Fructose and mannose metabolism, and substrate of phosphomannomutase 1 (PMM, EC: 5.4.2.8), an enzyme necessary for the synthesis of GDP-mannose. PMM converts mannose 6-phosphate to mannose-1-phosphate, which is required for the synthesis of GDP-mannose, a substrate for dolichol-linked oligosaccharide synthesis. 1-(Dihydrogen phosphate)-D-Mannopyranose 1-(Dihydrogen phosphate)-delta-Mannopyranose 1-(Dihydrogen phosphate)-δ-mannopyranose 1-(Dihydrogen phosphoric acid)-D-mannopyranose 1-(Dihydrogen phosphoric acid)-delta-mannopyranose 1-(Dihydrogen phosphoric acid)-δ-mannopyranose a-D-Mannose 1-phosphate a-D-Mannose 1-phosphoric acid a-delta-Mannose 1-phosphate a-delta-Mannose 1-phosphoric acid a-δ-Mannose 1-phosphate a-δ-Mannose 1-phosphoric acid Alpha-D-Mannose 1-phosphate alpha-D-Mannose 1-phosphoric acid Alpha-delta-Mannose 1-phosphate alpha-delta-Mannose 1-phosphoric acid D-Mannose 1-phosphates D-Mannose 1-phosphoric acid D-Mannose-1-phosphate D-Mannose-1-phosphoric acid Delta-Mannose 1-phosphates Delta-Mannose-1-phosphate delta-Mannose-1-phosphoric acid Man1P Mannose 1-phosphate Mannose 1-phosphate-Mannopyranose Mannose 1-phosphoric acid Mannose 1-phosphoric acid-mannopyranose Mannose-1-P Mannose-1-phosphate Mannose-1-phosphoric acid α-D-Mannose 1-phosphate α-D-Mannose 1-phosphoric acid α-δ-Mannose 1-phosphate α-δ-Mannose 1-phosphoric acid δ-Mannose 1-phosphates δ-Mannose-1-phosphate δ-Mannose-1-phosphoric acid C6H13O9P 260.1358 260.029718526 {[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid D-mannose 1-phosphate 27251-84-9 OC[C@H]1OC(OP(O)(O)=O)[C@@H](O)[C@@H](O)[C@@H]1O InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6?/m1/s1 HXXFSFRBOHSIMQ-QTVWNMPRSA-N Solid Cytosol logp -2.00 ALOGPS logs -0.91 ALOGPS solubility 3.23e+01 g/l ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 1.16 ChemAxon pka_strongest_basic -3 ChemAxon iupac {[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid ChemAxon average_mass 260.1358 ChemAxon mono_mass 260.029718526 ChemAxon smiles OC[C@H]1OC(OP(O)(O)=O)[C@@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C6H13O9P ChemAxon inchi InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6?/m1/s1 ChemAxon inchikey HXXFSFRBOHSIMQ-QTVWNMPRSA-N ChemAxon polar_surface_area 156.91 ChemAxon refractivity 46.8 ChemAxon polarizability 20.68 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 8 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Fructose and mannose metabolism ec00051 Amino sugar and nucleotide sugar metabolism ec00520 Metabolic pathways eco01100 Mannose Metabolism D-mannose can serve as a total source of carbon and energy for growth of E. coli. Alpha-D-mannose is introduced into the cytoplasm through a mannose PTS permease. Because mannose is taken up via a phosphotransferase system (PTS), the first intracellular species is D-mannose-6-phosphate. mannose-6-phosphate isomerase converts D-mannose-6-phosphate to D-fructose-6-phosphate, an intermediate of glycolysis, and hence it flows through the pathways of central metabolism to satisfy the cell's need for precursor metabolites, reducing power, and metabolic energy. The first two enzymes in the pathway (SEE VERTICAL SECTION) catalyze isomerizations that interconvert phosphorylated aldohexoses (β-D-glucose-6-phosphate, D-mannose-6-phosphate) and phosphorylated ketohexoses (D-fructose-6-phosphate). The reaction catalyzed by mannose-6-phosphate isomerase that produces D-mannose-6-phosphate is the first committed step in the biosynthesis of the activated mannose donor GDP-α-D-mannose. D-mannose-6-phosphate is then converted to GDP-D-mannose by the interaction of phosphomannomutase and mannose-1-phosphate guanylyltransferase . As for the bottom part L-fucose is biosynthesized as the sugar nucleotide GDP-L-fucose. Its biosynthesis from GDP-D-mannose begins with dehydration of this compound to GDP-4-dehydro-6-deoxy-D-mannose by the product of gene gmd. Then the bifunctional GDP-fucose synthase catalyzes the two-step (epimerase/reductase) synthesis of GDP-fucose from GDP-4-dehydro-6-deoxy-D-mannose via a GDP-4-dehydro-6-L-deoxygalactose intermediate. L-fucose is then incorporated into the colanic acid building blocks biosynthesis pathway. PW000822 Metabolic GDP-mannose biosynthesis PWY-5659 Specdb::CMs 1888 Specdb::CMs 3269 Specdb::CMs 31538 Specdb::CMs 39000 Specdb::NmrOneD 269998 Specdb::NmrOneD 269999 Specdb::NmrOneD 270000 Specdb::NmrOneD 270001 Specdb::NmrOneD 270002 Specdb::NmrOneD 270003 Specdb::NmrOneD 270004 Specdb::NmrOneD 270005 Specdb::NmrOneD 270006 Specdb::NmrOneD 270007 Specdb::NmrOneD 270008 Specdb::NmrOneD 270009 Specdb::NmrOneD 270010 Specdb::NmrOneD 270011 Specdb::NmrOneD 270012 Specdb::NmrOneD 270013 Specdb::NmrOneD 270014 Specdb::NmrOneD 270015 Specdb::NmrOneD 270016 Specdb::NmrOneD 270017 Specdb::MsMs 23165 Specdb::MsMs 23166 Specdb::MsMs 23167 Specdb::MsMs 29963 Specdb::MsMs 29964 Specdb::MsMs 29965 HMDB06330 644175 559210 C00636 35374 MANNOSE-1P 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. 21097882 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. 22080510 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. 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. 18331064 Korner C, Lehle L, von Figura K: Abnormal synthesis of mannose 1-phosphate derived carbohydrates in carbohydrate-deficient glycoprotein syndrome type I fibroblasts with phosphomannomutase deficiency. Glycobiology. 1998 Feb;8(2):165-71. 9451026 Van Schaftingen E, Jaeken J: Phosphomannomutase deficiency is a cause of carbohydrate-deficient glycoprotein syndrome type I. FEBS Lett. 1995 Dec 27;377(3):318-20. 8549746 Orvisky E, Stubblefield B, Long RT, Martin BM, Sidransky E, Krasnewich D: Phosphomannomutase activity in congenital disorders of glycosylation type Ia determined by direct analysis of the interconversion of mannose-1-phosphate to mannose-6-phosphate by high-pH anion-exchange chromatography with pulsed amperometric detection. Anal Biochem. 2003 Jun 1;317(1):12-8. 12729595 Mannose-1-phosphate guanylyltransferase P24174 MANC_ECOLI manC http://ecmdb.ca/proteins/P24174.xml Phosphomannomutase P24175 MANB_ECOLI manB http://ecmdb.ca/proteins/P24175.xml GDP-mannose pyrophosphatase nudK P37128 NUDK_ECOLI nudK http://ecmdb.ca/proteins/P37128.xml D-Mannose 1-phosphate <> Mannose 6-phosphate R01818 PHOSMANMUT-RXN Guanosine diphosphate + Hydrogen ion + D-Mannose 1-phosphate > Guanosine diphosphate mannose + Phosphate Guanosine diphosphate mannose + Water > Guanosine monophosphate +2 Hydrogen ion + D-Mannose 1-phosphate RXN0-5108 Guanosine triphosphate + D-Mannose 1-phosphate <> Pyrophosphate + Guanosine diphosphate mannose R00885 2.7.7.13-RXN Mannose 6-phosphate <> D-Mannose 1-phosphate R01818 Guanosine diphosphate mannose + Water > Hydrogen ion + Guanosine monophosphate + D-Mannose 1-phosphate RXN0-5108 Hydrogen ion + D-Mannose 1-phosphate + Guanosine triphosphate > Guanosine diphosphate mannose + Pyrophosphate 2.7.7.13-RXN α-D-mannose 6-phosphate > D-Mannose 1-phosphate PW_R002960 D-Mannose 1-phosphate + Guanosine triphosphate + Hydrogen ion > Pyrophosphate + Guanosine diphosphate mannose PW_R002961 Guanosine triphosphate + D-Mannose 1-phosphate <> Pyrophosphate + Guanosine diphosphate mannose Guanosine triphosphate + D-Mannose 1-phosphate <> Pyrophosphate + Guanosine diphosphate mannose