2.02015-09-08 19:39:16 -06002016-09-13 16:36:10 -0600ECMDB24538M2MDB006655PGP(19:iso/15:0)PGP(19:iso/15:0) 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(19:iso/15:0), in particular, consists of one 17-methylocatdecanoyl chain to the C-1 atom, and one pentadecanoyl 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.C40H80O13P2831.015830.507416632[(2S)-2-hydroxy-3-({hydroxy[(2R)-3-[(17-methyloctadecanoyl)oxy]-2-(pentadecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphonic acid(2S)-2-hydroxy-3-{[hydroxy((2R)-3-[(17-methyloctadecanoyl)oxy]-2-(pentadecanoyloxy)propoxy)phosphoryl]oxy}propoxyphosphonic acid[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC(C)C)OC(=O)CCCCCCCCCCCCCCInChI=1S/C40H80O13P2/c1-4-5-6-7-8-9-10-15-19-22-25-28-31-40(43)53-38(35-52-55(47,48)51-33-37(41)32-50-54(44,45)46)34-49-39(42)30-27-24-21-18-16-13-11-12-14-17-20-23-26-29-36(2)3/h36-38,41H,4-35H2,1-3H3,(H,47,48)(H2,44,45,46)/t37-,38+/m0/s1ZQBXVICACZDHGO-QPPIDDCLSA-Nlogp6.78logs-6.08solubility6.85e-04 g/llogp11.55pka_strongest_acidic1.35pka_strongest_basic-3.4iupac[(2S)-2-hydroxy-3-({hydroxy[(2R)-3-[(17-methyloctadecanoyl)oxy]-2-(pentadecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphonic acidaverage_mass831.015mono_mass830.507416632smiles[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC(C)C)OC(=O)CCCCCCCCCCCCCCformulaC40H80O13P2inchiInChI=1S/C40H80O13P2/c1-4-5-6-7-8-9-10-15-19-22-25-28-31-40(43)53-38(35-52-55(47,48)51-33-37(41)32-50-54(44,45)46)34-49-39(42)30-27-24-21-18-16-13-11-12-14-17-20-23-26-29-36(2)3/h36-38,41H,4-35H2,1-3H3,(H,47,48)(H2,44,45,46)/t37-,38+/m0/s1inchikeyZQBXVICACZDHGO-QPPIDDCLSA-Npolar_surface_area195.35refractivity215.33polarizability97.19rotatable_bond_count43acceptor_count8donor_count4physiological_charge-3formal_charge0phospholipid biosynthesis (CL(15:0cyclo/15:0cyclo/19:0cycv8c/19:0cycv8c))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.
PW001789MetabolicSpecdb::MsMs27314Specdb::MsMs27315Specdb::MsMs27316Specdb::MsMs33872Specdb::MsMs33873Specdb::MsMs33874Yurtsever 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(19:iso/15:0) + Water >2 PG(19:iso/15:0) + PhosphatePW_R005756