2.0 2015-09-08 19:32:52 -0600 2015-12-09 17:05:06 -0700 ECMDB24444 M2MDB006561 PGP(12:0/12:0(3-OH)) PGP(12:0/12:0(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(12:0/12:0(3-OH)), in particular, consists of one dodecanoyl chain to the C-1 atom, and one 3-hydroxydodecanoyl 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. C30H60O14P2 706.744 706.345830608 [(2R)-3-({[(2R)-3-(dodecanoyloxy)-2-[(3-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid (2R)-3-{[(2R)-3-(dodecanoyloxy)-2-[(3-hydroxydodecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CC(O)CCCCCCCCC InChI=1S/C30H60O14P2/c1-3-5-7-9-11-12-14-16-18-20-29(33)40-24-28(25-43-46(38,39)42-23-27(32)22-41-45(35,36)37)44-30(34)21-26(31)19-17-15-13-10-8-6-4-2/h26-28,31-32H,3-25H2,1-2H3,(H,38,39)(H2,35,36,37)/t26?,27-,28-/m1/s1 HUWSGSFPGYJBAX-DXISBFFWSA-N logp 3.54 ALOGPS logs -4.57 ALOGPS solubility 1.89e-02 g/l ALOGPS logp 6.03 ChemAxon pka_strongest_acidic 1.35 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac [(2R)-3-({[(2R)-3-(dodecanoyloxy)-2-[(3-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid ChemAxon average_mass 706.744 ChemAxon mono_mass 706.345830608 ChemAxon smiles [H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CC(O)CCCCCCCCC ChemAxon formula C30H60O14P2 ChemAxon inchi InChI=1S/C30H60O14P2/c1-3-5-7-9-11-12-14-16-18-20-29(33)40-24-28(25-43-46(38,39)42-23-27(32)22-41-45(35,36)37)44-30(34)21-26(31)19-17-15-13-10-8-6-4-2/h26-28,31-32H,3-25H2,1-2H3,(H,38,39)(H2,35,36,37)/t26?,27-,28-/m1/s1 ChemAxon inchikey HUWSGSFPGYJBAX-DXISBFFWSA-N ChemAxon polar_surface_area 215.58 ChemAxon refractivity 170.89 ChemAxon polarizability 77.12 ChemAxon rotatable_bond_count 34 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon phospholipid biosynthesis (CL(12:0(3-OH)/12:0(3-OH)/12:0/12:0)) 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. PW001915 Metabolic Specdb::CMs 1085718 Specdb::MsMs 1324429 Specdb::MsMs 1324430 Specdb::MsMs 1324431 Specdb::MsMs 1438795 Specdb::MsMs 1438796 Specdb::MsMs 1438797 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(12:0/12:0(3-OH)) + Water >2 PG(12:0/12:0(3-OH)) + Phosphate PW_R005763