2.0 2015-09-08 19:39:16 -0600 2016-09-13 16:36:10 -0600 ECMDB24538 M2MDB006655 PGP(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. C40H80O13P2 831.015 830.507416632 [(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)CCCCCCCCCCCCCC InChI=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/s1 ZQBXVICACZDHGO-QPPIDDCLSA-N logp 6.78 ALOGPS logs -6.08 ALOGPS solubility 6.85e-04 g/l ALOGPS logp 11.55 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2S)-2-hydroxy-3-({hydroxy[(2R)-3-[(17-methyloctadecanoyl)oxy]-2-(pentadecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphonic acid ChemAxon average_mass 831.015 ChemAxon mono_mass 830.507416632 ChemAxon smiles [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC(C)C)OC(=O)CCCCCCCCCCCCCC ChemAxon formula C40H80O13P2 ChemAxon inchi InChI=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/s1 ChemAxon inchikey ZQBXVICACZDHGO-QPPIDDCLSA-N ChemAxon polar_surface_area 195.35 ChemAxon refractivity 215.33 ChemAxon polarizability 97.19 ChemAxon rotatable_bond_count 43 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid 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. PW001789 Metabolic Specdb::MsMs 27314 Specdb::MsMs 27315 Specdb::MsMs 27316 Specdb::MsMs 33872 Specdb::MsMs 33873 Specdb::MsMs 33874 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:iso/15:0) + Water >2 PG(19:iso/15:0) + Phosphate PW_R005756