2.02015-09-08 19:33:29 -06002015-12-09 17:18:53 -0700ECMDB24457M2MDB006574PGP(14:0(3-OH)/17:0cycw7c)PGP(14:0(3-OH)/17:0cycw7c) 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(14:0(3-OH)/17:0cycw7c), in particular, consists of one 3-hydroxytetradecanoyl chain to the C-1 atom, and one heptadec-9-10-cyclo-anoyl 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.C37H72O14P2802.917802.439730994[(2R)-3-({[(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-[(3-hydroxytetradecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid(2R)-3-{[(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-[(3-hydroxytetradecanoyl)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)CCCCCCCCCCC)OC(=O)CCCCCCCC1CC1CCCCCCInChI=1S/C37H72O14P2/c1-3-5-7-9-10-11-12-15-19-23-33(38)26-37(41)47-29-35(30-50-53(45,46)49-28-34(39)27-48-52(42,43)44)51-36(40)24-20-16-13-14-18-22-32-25-31(32)21-17-8-6-4-2/h31-35,38-39H,3-30H2,1-2H3,(H,45,46)(H2,42,43,44)/t31?,32?,33?,34-,35-/m1/s1JTXBNJXFDWTZDB-IVHAPXLTSA-Nlogp5.28logs-5.64solubility1.83e-03 g/llogp8.36pka_strongest_acidic1.35pka_strongest_basic-2.8iupac[(2R)-3-({[(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-[(3-hydroxytetradecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acidaverage_mass802.917mono_mass802.439730994smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCCCC)OC(=O)CCCCCCCC1CC1CCCCCCformulaC37H72O14P2inchiInChI=1S/C37H72O14P2/c1-3-5-7-9-10-11-12-15-19-23-33(38)26-37(41)47-29-35(30-50-53(45,46)49-28-34(39)27-48-52(42,43)44)51-36(40)24-20-16-13-14-18-22-32-25-31(32)21-17-8-6-4-2/h31-35,38-39H,3-30H2,1-2H3,(H,45,46)(H2,42,43,44)/t31?,32?,33?,34-,35-/m1/s1inchikeyJTXBNJXFDWTZDB-IVHAPXLTSA-Npolar_surface_area215.58refractivity201.19polarizability89.22rotatable_bond_count39acceptor_count9donor_count5physiological_charge-3formal_charge0phospholipid biosynthesis (CL(14:0(3-OH)/17:0cycw7c/14:0(3-OH)/17:0cycw7c))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.PW001941MetabolicSpecdb::CMs1088632Specdb::NmrOneD276118Specdb::NmrOneD276119Specdb::NmrOneD276120Specdb::NmrOneD276121Specdb::NmrOneD276122Specdb::NmrOneD276123Specdb::NmrOneD276124Specdb::NmrOneD276125Specdb::NmrOneD276126Specdb::NmrOneD276127Specdb::NmrOneD276128Specdb::NmrOneD276129Specdb::NmrOneD276130Specdb::NmrOneD276131Specdb::NmrOneD276132Specdb::NmrOneD276133Specdb::NmrOneD276134Specdb::NmrOneD276135Specdb::NmrOneD276136Specdb::NmrOneD276137Specdb::MsMs1305550Specdb::MsMs1305551Specdb::MsMs1305552Specdb::MsMs1420069Specdb::MsMs1420070Specdb::MsMs1420071Yurtsever 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(14:0(3-OH)/17:0cycw7c) + Glycerol 3-phosphate >2 PGP(14:0(3-OH)/17:0cycw7c) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphatePW_R0054552 PGP(14:0(3-OH)/17:0cycw7c) + Water >2 PG(14:0(3-OH)/17:0cycw7c) + PhosphatePW_R005456