2.02015-09-08 19:33:00 -06002015-12-09 17:05:13 -0700ECMDB24447M2MDB006564PGP(14:0(3-OH)/10:0(3-OH))PGP(14:0(3-OH)/10:0(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(3-OH)/10:0(3-OH)), in particular, consists of one 3-hydroxytetradecanoyl chain to the C-1 atom, and one 3-hydroxydecanoyl 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.C30H60O15P2722.743722.340745228[(2R)-2-hydroxy-3-({hydroxy[(2R)-2-[(3-hydroxydecanoyl)oxy]-3-[(3-hydroxytetradecanoyl)oxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid(2R)-2-hydroxy-3-{[hydroxy((2R)-2-[(3-hydroxydecanoyl)oxy]-3-[(3-hydroxytetradecanoyl)oxy]propoxy)phosphoryl]oxy}propoxyphosphonic acid[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCCCC)OC(=O)CC(O)CCCCCCCInChI=1S/C30H60O15P2/c1-3-5-7-9-10-11-12-14-16-17-25(31)19-29(34)41-23-28(45-30(35)20-26(32)18-15-13-8-6-4-2)24-44-47(39,40)43-22-27(33)21-42-46(36,37)38/h25-28,31-33H,3-24H2,1-2H3,(H,39,40)(H2,36,37,38)/t25?,26?,27-,28-/m1/s1UIVGFOXEBOFEMN-XQOSCOKLSA-Nlogp2.80logs-4.23solubility4.25e-02 g/llogp4.8pka_strongest_acidic1.35pka_strongest_basic-2.8iupac[(2R)-2-hydroxy-3-({hydroxy[(2R)-2-[(3-hydroxydecanoyl)oxy]-3-[(3-hydroxytetradecanoyl)oxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acidaverage_mass722.743mono_mass722.340745228smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCCCC)OC(=O)CC(O)CCCCCCCformulaC30H60O15P2inchiInChI=1S/C30H60O15P2/c1-3-5-7-9-10-11-12-14-16-17-25(31)19-29(34)41-23-28(45-30(35)20-26(32)18-15-13-8-6-4-2)24-44-47(39,40)43-22-27(33)21-42-46(36,37)38/h25-28,31-33H,3-24H2,1-2H3,(H,39,40)(H2,36,37,38)/t25?,26?,27-,28-/m1/s1inchikeyUIVGFOXEBOFEMN-XQOSCOKLSA-Npolar_surface_area235.81refractivity172.4polarizability77.35rotatable_bond_count34acceptor_count10donor_count6physiological_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::CMs1086511Specdb::MsMs1298152Specdb::MsMs1298153Specdb::MsMs1298154Specdb::MsMs1412767Specdb::MsMs1412768Specdb::MsMs1412769Yurtsever 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(3-OH)/10:0(3-OH)) + Water >2 PG(14:0(3-OH)/10:0(3-OH)) + PhosphatePW_R005719