2.02015-09-08 19:32:36 -06002015-12-09 17:18:35 -0700ECMDB24438M2MDB006555PGP(12:0(3-OH)/16:1(9Z))PGP(12:0(3-OH)/16:1(9Z)) 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(3-OH)/16:1(9Z)), in particular, consists of one 3-hydroxydodecanoyl chain to the C-1 atom, and one 9Z-hexadecenoyl 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.C34H66O14P2760.836760.392780801[(2R)-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(3-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid(2R)-3-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(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)CC(O)CCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCInChI=1S/C34H66O14P2/c1-3-5-7-9-11-12-13-14-15-16-18-20-22-24-33(37)48-32(29-47-50(42,43)46-27-31(36)26-45-49(39,40)41)28-44-34(38)25-30(35)23-21-19-17-10-8-6-4-2/h12-13,30-32,35-36H,3-11,14-29H2,1-2H3,(H,42,43)(H2,39,40,41)/b13-12-/t30?,31-,32-/m1/s1GJADBVNIWPYXGP-LGZFZSLRSA-Nlogp4.67logs-5.15solubility5.44e-03 g/llogp7.44pka_strongest_acidic1.35pka_strongest_basic-2.8iupac[(2R)-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(3-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acidaverage_mass760.836mono_mass760.392780801smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCformulaC34H66O14P2inchiInChI=1S/C34H66O14P2/c1-3-5-7-9-11-12-13-14-15-16-18-20-22-24-33(37)48-32(29-47-50(42,43)46-27-31(36)26-45-49(39,40)41)28-44-34(38)25-30(35)23-21-19-17-10-8-6-4-2/h12-13,30-32,35-36H,3-11,14-29H2,1-2H3,(H,42,43)(H2,39,40,41)/b13-12-/t30?,31-,32-/m1/s1inchikeyGJADBVNIWPYXGP-LGZFZSLRSA-Npolar_surface_area215.58refractivity190.41polarizability83.19rotatable_bond_count37acceptor_count9donor_count5physiological_charge-3formal_charge0phospholipid biosynthesis (CL(16:1(9Z)/12:0/12:0/12:0))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.PW001955MetabolicSpecdb::CMs1087886Specdb::NmrOneD251748Specdb::NmrOneD251749Specdb::NmrOneD251750Specdb::NmrOneD251751Specdb::NmrOneD251752Specdb::NmrOneD251753Specdb::NmrOneD251754Specdb::NmrOneD251755Specdb::NmrOneD251756Specdb::NmrOneD251757Specdb::NmrOneD251758Specdb::NmrOneD251759Specdb::NmrOneD251760Specdb::NmrOneD251761Specdb::NmrOneD251762Specdb::NmrOneD251763Specdb::NmrOneD251764Specdb::NmrOneD251765Specdb::NmrOneD251766Specdb::NmrOneD251767Specdb::MsMs1271131Specdb::MsMs1271132Specdb::MsMs1271133Specdb::MsMs1386139Specdb::MsMs1386140Specdb::MsMs1386141Yurtsever 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(12:0(3-OH)/16:1(9Z)) + Water >2 PG(12:0(3-OH)/16:1(9Z)) + PhosphatePW_R005766