2.0 2015-09-08 19:31:23 -0600 2015-12-09 17:04:41 -0700 ECMDB24412 M2MDB006529 PGP(10:0(3-OH)/10:0) PGP(10:0(3-OH)/10:0) 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(10:0(3-OH)/10:0), in particular, consists of one 3-hydroxydecanoyl chain to the C-1 atom, and one decanoyl 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. C26H52O14P2 650.636 650.28323035 [(2R)-3-({[(2R)-2-(decanoyloxy)-3-[(3-hydroxydecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid (2R)-3-{[(2R)-2-(decanoyloxy)-3-[(3-hydroxydecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCC)OC(=O)CCCCCCCCC InChI=1S/C26H52O14P2/c1-3-5-7-9-10-12-14-16-25(29)40-24(20-36-26(30)17-22(27)15-13-11-8-6-4-2)21-39-42(34,35)38-19-23(28)18-37-41(31,32)33/h22-24,27-28H,3-21H2,1-2H3,(H,34,35)(H2,31,32,33)/t22?,23-,24-/m1/s1 AWWDWBXADRBUNK-HEYJASKDSA-N logp 2.39 ALOGPS logs -3.58 ALOGPS solubility 1.69e-01 g/l ALOGPS logp 4.25 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac [(2R)-3-({[(2R)-2-(decanoyloxy)-3-[(3-hydroxydecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid ChemAxon average_mass 650.636 ChemAxon mono_mass 650.28323035 ChemAxon smiles [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCC)OC(=O)CCCCCCCCC ChemAxon formula C26H52O14P2 ChemAxon inchi InChI=1S/C26H52O14P2/c1-3-5-7-9-10-12-14-16-25(29)40-24(20-36-26(30)17-22(27)15-13-11-8-6-4-2)21-39-42(34,35)38-19-23(28)18-37-41(31,32)33/h22-24,27-28H,3-21H2,1-2H3,(H,34,35)(H2,31,32,33)/t22?,23-,24-/m1/s1 ChemAxon inchikey AWWDWBXADRBUNK-HEYJASKDSA-N ChemAxon polar_surface_area 215.58 ChemAxon refractivity 152.49 ChemAxon polarizability 67.67 ChemAxon rotatable_bond_count 30 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(10:0(3-OH)/10:0/10:0(3-OH)/10:0)) 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. PW001899 Metabolic Specdb::CMs 1085196 Specdb::MsMs 1269436 Specdb::MsMs 1269437 Specdb::MsMs 1269438 Specdb::MsMs 1384459 Specdb::MsMs 1384460 Specdb::MsMs 1384461 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 CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase P0ABF8 PGSA_ECOLI pgsA http://ecmdb.ca/proteins/P0ABF8.xml Phosphatidylglycerophosphatase A P18200 PGPA_ECOLI pgpA http://ecmdb.ca/proteins/P18200.xml 2 CDP-DG(10:0(3-OH)/10:0) + Glycerol 3-phosphate >2 PGP(10:0(3-OH)/10:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate PW_R005282 2 PGP(10:0(3-OH)/10:0) + Water >2 PG(10:0(3-OH)/10:0) + Phosphate PW_R005283