2.02015-09-08 18:59:32 -06002015-12-09 12:07:40 -0700ECMDB24266M2MDB006383PG(16:1(9Z)/12:0)PG(16:1(9Z)/12:0) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(16:1(9Z)/12:0), in particular, consists of one 9Z-hexadecenoyl chain to the C-1 atom, and one dodecanoyl to the C-2 atom. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes.C34H65O10P664.858664.431535291[(2S)-2,3-dihydroxypropoxy][(2R)-3-(dodecanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propoxy]phosphinic acid(2S)-2,3-dihydroxypropoxy((2R)-3-(dodecanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propoxy)phosphinic acid[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCInChI=1S/C34H65O10P/c1-3-5-7-9-11-13-14-15-16-18-20-22-24-26-34(38)44-32(30-43-45(39,40)42-28-31(36)27-35)29-41-33(37)25-23-21-19-17-12-10-8-6-4-2/h13-14,31-32,35-36H,3-12,15-30H2,1-2H3,(H,39,40)/b14-13-/t31-,32+/m0/s1WXOIAUMPJKJVKS-BGCJVFQUSA-Nlogp6.75logs-6.33solubility3.08e-04 g/llogp8.8pka_strongest_acidic1.89pka_strongest_basic-3iupac[(2S)-2,3-dihydroxypropoxy][(2R)-3-(dodecanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propoxy]phosphinic acidaverage_mass664.858mono_mass664.431535291smiles[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCformulaC34H65O10PinchiInChI=1S/C34H65O10P/c1-3-5-7-9-11-13-14-15-16-18-20-22-24-26-34(38)44-32(30-43-45(39,40)42-28-31(36)27-35)29-41-33(37)25-23-21-19-17-12-10-8-6-4-2/h13-14,31-32,35-36H,3-12,15-30H2,1-2H3,(H,39,40)/b14-13-/t31-,32+/m0/s1inchikeyWXOIAUMPJKJVKS-BGCJVFQUSA-Npolar_surface_area148.82refractivity178.02polarizability77.41rotatable_bond_count35acceptor_count6donor_count3physiological_charge-1formal_charge0phospholipid biosynthesis (CL(16:1(9Z)/12:0/12:0/12:0))Phospholipids are membrane components in E. coli.
The major phospholipids of E. coli are phosphatidylethanolamine, phosphatidylglycerol and cardiolipin. All phospholipids contain sn-glycerol-3-phosphate esterified with fatty acids at the sn-1 and sn-2 positions.
The reaction starts from a glycerone phosphate (dihydroxyacetone phosphate) produced in glycolysis. The glycerone phosphate is transformed to a sn-glycerol 3-phosphate (glycerol 3 phosphate) by NADPH driven glycerol-3-phosphate dehydrogenase.
Sn-glycerol 3-phosphate is transformed to a 1-acyl-sn-glycerol 3-phosphate(1-oleyl-2-lyso-phosphatidate , 1-palmitoylglycerol 3-phosphate , 1-stearoyl-sn-glycerol 3-phosphate). This can be achieve by a sn-glycerol-3-phosphate 1-0-acyltransferase that interacts either with a long-chain acyl-CoA or with an acyl-[acp]. The 1-acyl-sn-glycerol 3-phosphate is transformed into a 1,2-diacyl-sn-glycerol 3-phosphate through a 1-acylglycerol-3-phosphate O-acyltransferase.
This compound is then converted into a CPD-diacylglycerol through a CTP (phosphatidate cytididyltransferase. CPD-diacylglycerol can be transformed either to a L-1-phosphatidylserine or a L-1-phosphatidylglycerol-phosphate through a phosphatidylserine synthase or a phosphatidylglycerophosphate synthase respectively. The L-1-phosphatidylserine transforms into L-1-phosphatidylethanolamine through a phosphatidylserine decarboxylase, o the other hand L-1-phosphatidylglycerol-phosphate gets transformed into a L-1-phosphatidyl-glycerol through a phosphatidylglycerophosphatase. These 2 products combines produce a cardiolipin and a ethanolamine.
The L-1 phosphatidyl-glycerol can also interact with cardiolipin synthase resulting in a glycerol and a cardiolipin.PW001955MetabolicSpecdb::CMs1084784Specdb::MsMs1263970Specdb::MsMs1263971Specdb::MsMs1263972Specdb::MsMs1379056Specdb::MsMs1379057Specdb::MsMs1379058Keseler, 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-D590.21097882Kanehisa, 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-D114.22080510Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75.22102590Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.APhosphatidylglycerophosphatase BP0A924PGPB_ECOLIpgpBhttp://ecmdb.ca/proteins/P0A924.xmlPhosphatidylglycerophosphatase AP18200PGPA_ECOLIpgpAhttp://ecmdb.ca/proteins/P18200.xml2 PGP(16:1(9Z)/12:0) + Water >2 PG(16:1(9Z)/12:0) + PhosphatePW_R005767