2.02015-09-08 19:32:47 -06002016-09-13 16:36:03 -0600ECMDB24442M2MDB006559PGP(12:0(3-OH)/19:iso)PGP(12:0(3-OH)/19:iso) 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)/19:iso), in particular, consists of one 3-hydroxydodecanoyl chain to the C-1 atom, and one 17-methylocatdecanoyl 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.C37H74O14P2804.933804.455381059[(2S)-2-hydroxy-3-({hydroxy[(2R)-3-[(3-hydroxydodecanoyl)oxy]-2-[(17-methyloctadecanoyl)oxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid(2S)-2-hydroxy-3-{[hydroxy((2R)-3-[(3-hydroxydodecanoyl)oxy]-2-[(17-methyloctadecanoyl)oxy]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)CCCCCCCCCCCCCCCC(C)CInChI=1S/C37H74O14P2/c1-4-5-6-7-15-19-22-25-33(38)27-37(41)47-30-35(31-50-53(45,46)49-29-34(39)28-48-52(42,43)44)51-36(40)26-23-20-17-14-12-10-8-9-11-13-16-18-21-24-32(2)3/h32-35,38-39H,4-31H2,1-3H3,(H,45,46)(H2,42,43,44)/t33?,34-,35+/m0/s1CHESALVBLJYTOC-ZYVKZGOESA-Nlogp5.27logs-5.63solubility1.89e-03 g/llogp8.98pka_strongest_acidic1.35pka_strongest_basic-2.8iupac[(2S)-2-hydroxy-3-({hydroxy[(2R)-3-[(3-hydroxydodecanoyl)oxy]-2-[(17-methyloctadecanoyl)oxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acidaverage_mass804.933mono_mass804.455381059smiles[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCC(C)CformulaC37H74O14P2inchiInChI=1S/C37H74O14P2/c1-4-5-6-7-15-19-22-25-33(38)27-37(41)47-30-35(31-50-53(45,46)49-29-34(39)28-48-52(42,43)44)51-36(40)26-23-20-17-14-12-10-8-9-11-13-16-18-21-24-32(2)3/h32-35,38-39H,4-31H2,1-3H3,(H,45,46)(H2,42,43,44)/t33?,34-,35+/m0/s1inchikeyCHESALVBLJYTOC-ZYVKZGOESA-Npolar_surface_area215.58refractivity203.04polarizability91.3rotatable_bond_count40acceptor_count9donor_count5physiological_charge-3formal_charge0phospholipid biosynthesis (CL(12:0(3-OH)/19:iso/12:0(3-OH)/19:iso))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.
PW001926MetabolicSpecdb::CMs1085488Specdb::NmrOneD282869Specdb::NmrOneD282870Specdb::NmrOneD282871Specdb::NmrOneD282872Specdb::NmrOneD282873Specdb::NmrOneD282874Specdb::NmrOneD282875Specdb::NmrOneD282876Specdb::NmrOneD282877Specdb::NmrOneD282878Specdb::NmrOneD282879Specdb::NmrOneD282880Specdb::NmrOneD282881Specdb::NmrOneD282882Specdb::NmrOneD282883Specdb::NmrOneD282884Specdb::NmrOneD282885Specdb::NmrOneD282886Specdb::NmrOneD282887Specdb::NmrOneD282888Specdb::MsMs23627Specdb::MsMs23628Specdb::MsMs23629Specdb::MsMs30425Specdb::MsMs30426Specdb::MsMs30427Yurtsever 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)/19:iso) + Glycerol 3-phosphate >2 PGP(12:0(3-OH)/19:iso) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphatePW_R0053972 PGP(12:0(3-OH)/19:iso) + Water >2 PG(12:0(3-OH)/19:iso) + PhosphatePW_R005398