2.02015-09-08 19:32:41 -06002015-12-09 17:18:41 -0700ECMDB24440M2MDB006557PGP(12:0(3-OH)/18:1(9Z))PGP(12:0(3-OH)/18:1(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)/18:1(9Z)), in particular, consists of one 3-hydroxydodecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl 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.C36H70O14P2788.89788.42408093[(2R)-2-hydroxy-3-({hydroxy[(2R)-3-[(3-hydroxydodecanoyl)oxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid(2R)-2-hydroxy-3-{[hydroxy((2R)-3-[(3-hydroxydodecanoyl)oxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy)phosphoryl]oxy}propoxyphosphonic acid[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCCInChI=1S/C36H70O14P2/c1-3-5-7-9-11-12-13-14-15-16-17-18-20-22-24-26-35(39)50-34(31-49-52(44,45)48-29-33(38)28-47-51(41,42)43)30-46-36(40)27-32(37)25-23-21-19-10-8-6-4-2/h14-15,32-34,37-38H,3-13,16-31H2,1-2H3,(H,44,45)(H2,41,42,43)/b15-14-/t32?,33-,34-/m1/s1OHXFLRNSMWLBJY-SHDUCQPMSA-Nlogp5.34logs-5.41solubility3.06e-03 g/llogp8.33pka_strongest_acidic1.35pka_strongest_basic-2.8iupac[(2R)-2-hydroxy-3-({hydroxy[(2R)-3-[(3-hydroxydodecanoyl)oxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acidaverage_mass788.89mono_mass788.42408093smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCCformulaC36H70O14P2inchiInChI=1S/C36H70O14P2/c1-3-5-7-9-11-12-13-14-15-16-17-18-20-22-24-26-35(39)50-34(31-49-52(44,45)48-29-33(38)28-47-51(41,42)43)30-46-36(40)27-32(37)25-23-21-19-10-8-6-4-2/h14-15,32-34,37-38H,3-13,16-31H2,1-2H3,(H,44,45)(H2,41,42,43)/b15-14-/t32?,33-,34-/m1/s1inchikeyOHXFLRNSMWLBJY-SHDUCQPMSA-Npolar_surface_area215.58refractivity199.61polarizability87.41rotatable_bond_count39acceptor_count9donor_count5physiological_charge-3formal_charge0phospholipid biosynthesis (CL(12:0(3-OH)/18:1(9Z)/12:0(3-OH)/18:1(9Z)))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.PW001924MetabolicSpecdb::CMs1087625Specdb::NmrOneD283409Specdb::NmrOneD283410Specdb::NmrOneD283411Specdb::NmrOneD283412Specdb::NmrOneD283413Specdb::NmrOneD283414Specdb::NmrOneD283415Specdb::NmrOneD283416Specdb::NmrOneD283417Specdb::NmrOneD283418Specdb::NmrOneD283419Specdb::NmrOneD283420Specdb::NmrOneD283421Specdb::NmrOneD283422Specdb::NmrOneD283423Specdb::NmrOneD283424Specdb::NmrOneD283425Specdb::NmrOneD283426Specdb::NmrOneD283427Specdb::NmrOneD283428Specdb::MsMs1291120Specdb::MsMs1291121Specdb::MsMs1291122Specdb::MsMs1405828Specdb::MsMs1405829Specdb::MsMs1405830Yurtsever 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.xmlCDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferaseP0ABF8PGSA_ECOLIpgsAhttp://ecmdb.ca/proteins/P0ABF8.xmlPhosphatidylglycerophosphatase AP18200PGPA_ECOLIpgpAhttp://ecmdb.ca/proteins/P18200.xml2 CDP-DG(12:0(3-OH)/18:1(9Z)) + Glycerol 3-phosphate >2 PGP(12:0(3-OH)/18:1(9Z)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphatePW_R0053892 PGP(12:0(3-OH)/18:1(9Z)) + Water >2 PG(12:0(3-OH)/18:1(9Z)) + PhosphatePW_R005390