2.0 2012-05-31 14:05:09 -0600 2015-06-03 15:54:44 -0600 ECMDB04104 M2MDB000612 2-C-Methyl-D-erythritol-4-phosphate 2-c-methyl-D-erythritol-4-phosphate is a member of the chemical class known as Tetroses. These are tetrasaccharides whose saccharide units are all hexoses. 2-C-methyl-D-erythritol-4-phosphate is involved in isoprenoid biosynthesis. Using genetically engineered Escherichia coli cells able to utilize exogenously provided mevalonate for isoprenoid biosynthesis by the mevalonate pathway we demonstrate that the lytB gene is involved in the trunk line of the MEP pathway. (PMID 11418107) The first step of the 2-C-methyl-D-erythritol 4-phosphate (MEP) pathway for isoprenoid biosynthesis in plant plastids and most eubacteria is catalyzed by 1-deoxy-D-xylulose 5-phosphate synthase (DXS), a recently described transketolase-like enzyme. (PMID 11708793) In the MEP pathway, 4-diphosphocytidyl-2-C-methyl-D-erythritol is formed from 2-C-methyl-D-erythritol 4-phosphate (MEP) and CTP in a reaction catalyzed by a 4-diphosphocytidyl-2-C-methyl-D-erythritol synthase (IspD). (PMID 17921290) (E)-4-Hydroxy-3-methylbut-2-enyl diphosphate synthase (GcpE), which catalyzes the conversion of 2-C-methyl-D-erythritol cyclodiphosphate (MEcPP) into (E)-4-hydroxy-3-methylbut-2-enyl diphosphate (HMBPP), is an essential enzyme of the non-mevalonate (2-C-methyl-D-erythritol-4-phosphate (MEP)) pathway for isoprenoid biosynthesis. (E)-4-Hydroxy-3-methylbut-2-enyl diphosphate synthase (GcpE), which catalyzes the conversion of 2-C-methyl-D-erythritol cyclodiphosphate (MEcPP) into (E)-4-hydroxy-3-methylbut-2-enyl diphosphate (HMBPP), is an essential enzyme of the non-mevalonate (2-C-methyl-D-erythritol-4-phosphate (MEP)) pathway for isoprenoid biosynthesis. (PMID 15792953) Escherichia coli AmtB is a member of the MEP/Amt family of ammonia transporters found in archaea, eubacteria, fungi, plants and animals. (PMID 12753193) 2-C-Methyl-D-erythritol-4-phosphate 2-C-Methyl-D-erythritol-4-phosphoric acid MeEry4P MEP C5H11O7P 214.1104 214.024239218 2-methyl-4-(phosphonatooxy)butane-1,2,3-triol 2-methyl-4-(phosphonatooxy)butane-1,2,3-triol CC(O)(CO)C(O)COP([O-])([O-])=O InChI=1S/C5H13O7P/c1-5(8,3-6)4(7)2-12-13(9,10)11/h4,6-8H,2-3H2,1H3,(H2,9,10,11)/p-2 XMWHRVNVKDKBRG-UHFFFAOYSA-L Cytosol logp -1.71 ALOGPS logs -0.56 ALOGPS solubility 6.93e+01 g/l ALOGPS logp -2.3 ChemAxon pka_strongest_acidic 1.49 ChemAxon pka_strongest_basic -3.1 ChemAxon iupac 2-methyl-4-(phosphonatooxy)butane-1,2,3-triol ChemAxon average_mass 214.1104 ChemAxon mono_mass 214.024239218 ChemAxon smiles CC(O)(CO)C(O)COP([O-])([O-])=O ChemAxon formula C5H11O7P ChemAxon inchi InChI=1S/C5H13O7P/c1-5(8,3-6)4(7)2-12-13(9,10)11/h4,6-8H,2-3H2,1H3,(H2,9,10,11)/p-2 ChemAxon inchikey XMWHRVNVKDKBRG-UHFFFAOYSA-L ChemAxon polar_surface_area 133.11 ChemAxon refractivity 39.75 ChemAxon polarizability 17.45 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge -2 ChemAxon Terpenoid backbone biosynthesis ec00900 Metabolic pathways eco01100 methylerythritol phosphate pathway NONMEVIPP-PWY Specdb::NmrOneD 283869 Specdb::NmrOneD 283870 Specdb::NmrOneD 283871 Specdb::NmrOneD 283872 Specdb::NmrOneD 283873 Specdb::NmrOneD 283874 Specdb::NmrOneD 283875 Specdb::NmrOneD 283876 Specdb::NmrOneD 283877 Specdb::NmrOneD 283878 Specdb::NmrOneD 283879 Specdb::NmrOneD 283880 Specdb::NmrOneD 283881 Specdb::NmrOneD 283882 Specdb::NmrOneD 283883 Specdb::NmrOneD 283884 Specdb::NmrOneD 283885 Specdb::NmrOneD 283886 Specdb::NmrOneD 283887 Specdb::NmrOneD 283888 Specdb::MsMs 23180 Specdb::MsMs 23181 Specdb::MsMs 23182 Specdb::MsMs 29978 Specdb::MsMs 29979 Specdb::MsMs 29980 21896402 10645747 C11434 17764 2-C-METHYL-D-ERYTHRITOL-4-PHOSPHATE 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 Querol, J., Rodriguez-Concepcion, M., Boronat, A., Imperial, S. (2001). "Essential role of residue H49 for activity of Escherichia coli 1-deoxy-D-xylulose 5-phosphate synthase, the enzyme catalyzing the first step of the 2-C-methyl-D-erythritol 4-phosphate pathway for isoprenoid Synthesis." Biochem Biophys Res Commun 289:155-160. 11708793 Blauwkamp, T. A., Ninfa, A. J. (2003). "Antagonism of PII signalling by the AmtB protein of Escherichia coli." Mol Microbiol 48:1017-1028. 12753193 Okada, K., Hase, T. (2005). "Cyanobacterial non-mevalonate pathway: (E)-4-hydroxy-3-methylbut-2-enyl diphosphate synthase interacts with ferredoxin in Thermosynechococcus elongatus BP-1." J Biol Chem 280:20672-20679. 15792953 Eoh, H., Brown, A. C., Buetow, L., Hunter, W. N., Parish, T., Kaur, D., Brennan, P. J., Crick, D. C. (2007). "Characterization of the Mycobacterium tuberculosis 4-diphosphocytidyl-2-C-methyl-D-erythritol synthase: potential for drug development." J Bacteriol 189:8922-8927. 17921290 1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI dxr http://ecmdb.ca/proteins/P45568.xml 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase Q46893 ISPD_ECOLI ispD http://ecmdb.ca/proteins/Q46893.xml 1-Deoxy-D-xylulose 5-phosphate + Hydrogen ion + NADPH <> 2-C-Methyl-D-erythritol-4-phosphate + NADP R05688 DXPREDISOM-RXN 2-C-Methyl-D-erythritol-4-phosphate + Cytidine triphosphate + Hydrogen ion <> 4-(Cytidine 5'-diphospho)-2-C-methyl-D-erythritol + Pyrophosphate R05633 2.7.7.60-RXN 2-C-Methyl-D-erythritol-4-phosphate + Cytidine triphosphate <> 4-(Cytidine 5'-diphospho)-2-C-methyl-D-erythritol + Pyrophosphate R05633 2-C-Methyl-D-erythritol-4-phosphate + NADP <> 1-Deoxy-D-xylulose 5-phosphate + NADPH + Hydrogen ion R05688 DXPREDISOM-RXN Hydrogen ion + 2-C-Methyl-D-erythritol-4-phosphate + Cytidine triphosphate > 4-(Cytidine 5'-diphospho)-2-C-methyl-D-erythritol + Pyrophosphate 2.7.7.60-RXN 1-Deoxy-D-xylulose 5-phosphate + Hydrogen ion + NADPH <>2 2-C-Methyl-D-erythritol-4-phosphate + NADP 1-Deoxy-D-xylulose 5-phosphate + Hydrogen ion + NADPH <>2 2-C-Methyl-D-erythritol-4-phosphate + NADP