2.02015-09-08 19:33:48 -06002015-12-09 17:19:08 -0700ECMDB24463M2MDB006580PGP(14:0/14:0(3-OH))PGP(14:0/14:0(3-OH)) belongs to the class of glycerophosphoglycerophosphates, also called phosphatidylglycerophosphates (PGPs). These lipids contain a common glycerophosphate skeleton linked to at least one fatty acyl chain and a glycero-3-phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PGP(14:0/14:0(3-OH)), in particular, consists of one tetradecanoyl chain to the C-1 atom, and one 3-hydroxytetradecanoyl to the C-2 atom. In E. coli, PGPs can be found in the cytoplasmic membrane. The are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to Phosphatidylglycerols (PGs) by the enzyme Phosphatidylglycerophosphatase.C34H68O14P2762.852762.408430866[(2R)-2-hydroxy-3-({hydroxy[(2R)-2-[(3-hydroxytetradecanoyl)oxy]-3-(tetradecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphonic acid(2R)-2-hydroxy-3-{[hydroxy((2R)-2-[(3-hydroxytetradecanoyl)oxy]-3-(tetradecanoyloxy)propoxy)phosphoryl]oxy}propoxyphosphonic acid[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CC(O)CCCCCCCCCCCInChI=1S/C34H68O14P2/c1-3-5-7-9-11-13-14-16-18-20-22-24-33(37)44-28-32(29-47-50(42,43)46-27-31(36)26-45-49(39,40)41)48-34(38)25-30(35)23-21-19-17-15-12-10-8-6-4-2/h30-32,35-36H,3-29H2,1-2H3,(H,42,43)(H2,39,40,41)/t30?,31-,32-/m1/s1OKUQRZQPPIGZEW-YPHBKRNWSA-Nlogp4.77logs-5.25solubility4.31e-03 g/llogp7.8pka_strongest_acidic1.35pka_strongest_basic-2.8iupac[(2R)-2-hydroxy-3-({hydroxy[(2R)-2-[(3-hydroxytetradecanoyl)oxy]-3-(tetradecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphonic acidaverage_mass762.852mono_mass762.408430866smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CC(O)CCCCCCCCCCCformulaC34H68O14P2inchiInChI=1S/C34H68O14P2/c1-3-5-7-9-11-13-14-16-18-20-22-24-33(37)44-28-32(29-47-50(42,43)46-27-31(36)26-45-49(39,40)41)48-34(38)25-30(35)23-21-19-17-15-12-10-8-6-4-2/h30-32,35-36H,3-29H2,1-2H3,(H,42,43)(H2,39,40,41)/t30?,31-,32-/m1/s1inchikeyOKUQRZQPPIGZEW-YPHBKRNWSA-Npolar_surface_area215.58refractivity189.29polarizability85.65rotatable_bond_count38acceptor_count9donor_count5physiological_charge-3formal_charge0phospholipid biosynthesis (CL(17:0cycw7c/10:0(3-OH)/14:0/14:0))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.
PW001966MetabolicSpecdb::CMs1088495Specdb::NmrOneD250928Specdb::NmrOneD250929Specdb::NmrOneD250930Specdb::NmrOneD250931Specdb::NmrOneD250932Specdb::NmrOneD250933Specdb::NmrOneD250934Specdb::NmrOneD250935Specdb::NmrOneD250936Specdb::NmrOneD250937Specdb::NmrOneD250938Specdb::NmrOneD250939Specdb::NmrOneD250940Specdb::NmrOneD250941Specdb::NmrOneD250942Specdb::NmrOneD250943Specdb::NmrOneD250944Specdb::NmrOneD250945Specdb::NmrOneD250946Specdb::NmrOneD250947Specdb::MsMs1306018Specdb::MsMs1306019Specdb::MsMs1306020Specdb::MsMs1420537Specdb::MsMs1420538Specdb::MsMs1420539Yurtsever 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(14:0/14:0(3-OH)) + Water >2 PG(14:0/14:0(3-OH)) + PhosphatePW_R005723