2.02015-09-08 19:36:47 -06002015-12-09 17:21:26 -0700ECMDB24515M2MDB006632PGP(19:0cycv8c/10:0(3-OH))PGP(19:0cycv8c/10:0(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(19:0cycv8c/10:0(3-OH)), in particular, consists of one heptadec-11-12-cyclo-anoyl chain to the C-1 atom, and one 3-hydroxydecanoyl 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.C35H68O14P2774.863774.408430866[(2R)-3-({[(2R)-3-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-2-[(3-hydroxydecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid(2R)-3-{[(2R)-3-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-2-[(3-hydroxydecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCC1CC1CCCCCC)OC(=O)CC(O)CCCCCCCInChI=1S/C35H68O14P2/c1-3-5-7-12-17-21-31(36)24-35(39)49-33(28-48-51(43,44)47-26-32(37)25-46-50(40,41)42)27-45-34(38)22-18-14-11-9-10-13-16-20-30-23-29(30)19-15-8-6-4-2/h29-33,36-37H,3-28H2,1-2H3,(H,43,44)(H2,40,41,42)/t29?,30?,31?,32-,33-/m1/s1IDCGKMILRXBVEV-CDWAUKDPSA-Nlogp4.76logs-5.43solubility2.85e-03 g/llogp7.47pka_strongest_acidic1.35pka_strongest_basic-2.8iupac[(2R)-3-({[(2R)-3-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-2-[(3-hydroxydecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acidaverage_mass774.863mono_mass774.408430866smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCC1CC1CCCCCC)OC(=O)CC(O)CCCCCCCformulaC35H68O14P2inchiInChI=1S/C35H68O14P2/c1-3-5-7-12-17-21-31(36)24-35(39)49-33(28-48-51(43,44)47-26-32(37)25-46-50(40,41)42)27-45-34(38)22-18-14-11-9-10-13-16-20-30-23-29(30)19-15-8-6-4-2/h29-33,36-37H,3-28H2,1-2H3,(H,43,44)(H2,40,41,42)/t29?,30?,31?,32-,33-/m1/s1inchikeyIDCGKMILRXBVEV-CDWAUKDPSA-Npolar_surface_area215.58refractivity191.99polarizability86.41rotatable_bond_count37acceptor_count9donor_count5physiological_charge-3formal_charge0phospholipid biosynthesis (CL(19:0cycv8c/10:0(3-OH)/10:0/10:0))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.
PW001989Metabolicphospholipid biosynthesis (CL(19:0cycv8c/10:0(3-OH)/19:0cycv8c/10:0(3-OH)))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.
PW001991MetabolicSpecdb::CMs1086222Specdb::EiMs4701Specdb::NmrOneD258448Specdb::NmrOneD258449Specdb::NmrOneD258450Specdb::NmrOneD258451Specdb::NmrOneD258452Specdb::NmrOneD258453Specdb::NmrOneD258454Specdb::NmrOneD258455Specdb::NmrOneD258456Specdb::NmrOneD258457Specdb::NmrOneD258458Specdb::NmrOneD258459Specdb::NmrOneD258460Specdb::NmrOneD258461Specdb::NmrOneD258462Specdb::NmrOneD258463Specdb::NmrOneD258464Specdb::NmrOneD258465Specdb::NmrOneD258466Specdb::NmrOneD258467Specdb::MsMs1285825Specdb::MsMs1285826Specdb::MsMs1285827Specdb::MsMs1400620Specdb::MsMs1400621Specdb::MsMs1400622Yurtsever 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(19:0cycv8c/10:0(3-OH)) + Glycerol 3-phosphate >2 PGP(19:0cycv8c/10:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphatePW_R0056032 PGP(19:0cycv8c/10:0(3-OH)) + Water >2 PG(19:0cycv8c/10:0(3-OH)) + PhosphatePW_R005604