2.0 2015-09-08 19:01:34 -0600 2015-12-09 17:04:18 -0700 ECMDB24318 M2MDB006435 PGP(19:0/17:0) PGP(19:0/17:0) 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(19:0/17:0), in particular, consists of one nonadecanoyl chain to the C-1 atom, and one heptadecanoyl 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. C42H84O13P2 859.069 858.538716761 [(2R)-3-({[(2R)-2-(heptadecanoyloxy)-3-(nonadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid (2R)-3-{[(2R)-2-(heptadecanoyloxy)-3-(nonadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCC InChI=1S/C42H84O13P2/c1-3-5-7-9-11-13-15-17-19-20-22-23-25-27-29-31-33-41(44)51-37-40(38-54-57(49,50)53-36-39(43)35-52-56(46,47)48)55-42(45)34-32-30-28-26-24-21-18-16-14-12-10-8-6-4-2/h39-40,43H,3-38H2,1-2H3,(H,49,50)(H2,46,47,48)/t39-,40-/m1/s1 PBRMXDCOVPAGKN-XRSDMRJBSA-N logp 7.47 ALOGPS logs -6.25 ALOGPS solubility 4.87e-04 g/l ALOGPS logp 12.59 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2R)-3-({[(2R)-2-(heptadecanoyloxy)-3-(nonadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid ChemAxon average_mass 859.069 ChemAxon mono_mass 858.538716761 ChemAxon smiles [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCC ChemAxon formula C42H84O13P2 ChemAxon inchi InChI=1S/C42H84O13P2/c1-3-5-7-9-11-13-15-17-19-20-22-23-25-27-29-31-33-41(44)51-37-40(38-54-57(49,50)53-36-39(43)35-52-56(46,47)48)55-42(45)34-32-30-28-26-24-21-18-16-14-12-10-8-6-4-2/h39-40,43H,3-38H2,1-2H3,(H,49,50)(H2,46,47,48)/t39-,40-/m1/s1 ChemAxon inchikey PBRMXDCOVPAGKN-XRSDMRJBSA-N ChemAxon polar_surface_area 195.35 ChemAxon refractivity 224.59 ChemAxon polarizability 101.84 ChemAxon rotatable_bond_count 46 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(19:iso/17:0cycw7c/19:0/19:0)) 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. PW002007 Metabolic Specdb::MsMs 1240744 Specdb::MsMs 1240745 Specdb::MsMs 1240746 Specdb::MsMs 1356160 Specdb::MsMs 1356161 Specdb::MsMs 1356162 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A Phosphatidylglycerophosphatase B P0A924 PGPB_ECOLI pgpB http://ecmdb.ca/proteins/P0A924.xml Phosphatidylglycerophosphatase A P18200 PGPA_ECOLI pgpA http://ecmdb.ca/proteins/P18200.xml 2 PGP(19:0/17:0) + Water >2 PG(19:0/17:0) + Phosphate PW_R005803