2.02015-09-08 19:38:30 -06002016-09-13 16:36:09 -0600ECMDB24532M2MDB006649PGP(19:iso/10:0(3-OH))PGP(19:iso/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:iso/10:0(3-OH)), in particular, consists of one 17-methylocatdecanoyl 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.C35H70O14P2776.879776.42408093[(2S)-2-hydroxy-3-({hydroxy[(2R)-2-[(3-hydroxydecanoyl)oxy]-3-[(17-methyloctadecanoyl)oxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid(2S)-2-hydroxy-3-{[hydroxy((2R)-2-[(3-hydroxydecanoyl)oxy]-3-[(17-methyloctadecanoyl)oxy]propoxy)phosphoryl]oxy}propoxyphosphonic acid[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC(C)C)OC(=O)CC(O)CCCCCCCInChI=1S/C35H70O14P2/c1-4-5-6-16-20-23-31(36)25-35(39)49-33(29-48-51(43,44)47-27-32(37)26-46-50(40,41)42)28-45-34(38)24-21-18-15-13-11-9-7-8-10-12-14-17-19-22-30(2)3/h30-33,36-37H,4-29H2,1-3H3,(H,43,44)(H2,40,41,42)/t31?,32-,33+/m0/s1TYYGITZUMMNIGV-ADIDXWPESA-Nlogp4.88logs-5.43solubility2.90e-03 g/llogp8.09pka_strongest_acidic1.35pka_strongest_basic-2.8iupac[(2S)-2-hydroxy-3-({hydroxy[(2R)-2-[(3-hydroxydecanoyl)oxy]-3-[(17-methyloctadecanoyl)oxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acidaverage_mass776.879mono_mass776.42408093smiles[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC(C)C)OC(=O)CC(O)CCCCCCCformulaC35H70O14P2inchiInChI=1S/C35H70O14P2/c1-4-5-6-16-20-23-31(36)25-35(39)49-33(29-48-51(43,44)47-27-32(37)26-46-50(40,41)42)28-45-34(38)24-21-18-15-13-11-9-7-8-10-12-14-17-19-22-30(2)3/h30-33,36-37H,4-29H2,1-3H3,(H,43,44)(H2,40,41,42)/t31?,32-,33+/m0/s1inchikeyTYYGITZUMMNIGV-ADIDXWPESA-Npolar_surface_area215.58refractivity193.84polarizability87.48rotatable_bond_count38acceptor_count9donor_count5physiological_charge-3formal_charge0phospholipid biosynthesis (CL(19:iso/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.
PW001996Metabolicphospholipid biosynthesis (CL(19:iso/10:0(3-OH)/19:iso/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.
PW001997MetabolicSpecdb::CMs1085386Specdb::NmrOneD334898Specdb::NmrOneD334899Specdb::NmrOneD334900Specdb::NmrOneD334901Specdb::NmrOneD334902Specdb::NmrOneD334903Specdb::NmrOneD334904Specdb::NmrOneD334905Specdb::NmrOneD334906Specdb::NmrOneD334907Specdb::NmrOneD334908Specdb::NmrOneD334909Specdb::NmrOneD334910Specdb::NmrOneD334911Specdb::NmrOneD334912Specdb::NmrOneD334913Specdb::NmrOneD334914Specdb::NmrOneD334915Specdb::NmrOneD334916Specdb::NmrOneD334917Specdb::MsMs24947Specdb::MsMs24948Specdb::MsMs24949Specdb::MsMs31505Specdb::MsMs31506Specdb::MsMs31507Yurtsever 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:iso/10:0(3-OH)) + Glycerol 3-phosphate >2 PGP(19:iso/10:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphatePW_R0056212 PGP(19:iso/10:0(3-OH)) + Water >2 PG(19:iso/10:0(3-OH)) + PhosphatePW_R005622