2.02015-09-08 19:01:37 -06002015-12-09 17:04:19 -0700ECMDB24319M2MDB006436PGP(19:0/18:1(11Z))PGP(19:0/18:1(11Z)) 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(19:0/18:1(11Z)), in particular, consists of one nonadecanoyl chain to the C-1 atom, and one 11Z-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.C43H84O13P2871.08870.538716761[(2R)-2-hydroxy-3-({hydroxy[(2R)-3-(nonadecanoyloxy)-2-[(11Z)-octadec-11-enoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid(2R)-2-hydroxy-3-{[hydroxy((2R)-3-(nonadecanoyloxy)-2-[(11Z)-octadec-11-enoyloxy]propoxy)phosphoryl]oxy}propoxyphosphonic acid[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCCInChI=1S/C43H84O13P2/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-42(45)52-38-41(39-55-58(50,51)54-37-40(44)36-53-57(47,48)49)56-43(46)35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h14,16,40-41,44H,3-13,15,17-39H2,1-2H3,(H,50,51)(H2,47,48,49)/b16-14-/t40-,41-/m1/s1XHQNUGBNLJRWNH-RHYWPTEDSA-Nlogp7.68logs-6.25solubility4.86e-04 g/llogp12.67pka_strongest_acidic1.35pka_strongest_basic-3.4iupac[(2R)-2-hydroxy-3-({hydroxy[(2R)-3-(nonadecanoyloxy)-2-[(11Z)-octadec-11-enoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acidaverage_mass871.08mono_mass870.538716761smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCCformulaC43H84O13P2inchiInChI=1S/C43H84O13P2/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-42(45)52-38-41(39-55-58(50,51)54-37-40(44)36-53-57(47,48)49)56-43(46)35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h14,16,40-41,44H,3-13,15,17-39H2,1-2H3,(H,50,51)(H2,47,48,49)/b16-14-/t40-,41-/m1/s1inchikeyXHQNUGBNLJRWNH-RHYWPTEDSA-Npolar_surface_area195.35refractivity230.3polarizability102.6rotatable_bond_count46acceptor_count8donor_count4physiological_charge-3formal_charge0phospholipid biosynthesis (CL(19:0/18:1(11Z)/14:0/14:0))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.
PW001986Metabolicphospholipid biosynthesis (CL(19:0/18:1(11Z)/19:0/18:1(11Z)))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.
PW001987Metabolicphospholipid biosynthesis (CL(19:0/18:1(11Z)/19:0/19:0))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.
PW001988MetabolicSpecdb::NmrOneD286075Specdb::NmrOneD286076Specdb::NmrOneD286077Specdb::NmrOneD286078Specdb::NmrOneD286079Specdb::NmrOneD286080Specdb::NmrOneD286081Specdb::NmrOneD286082Specdb::NmrOneD286083Specdb::NmrOneD286084Specdb::NmrOneD286085Specdb::NmrOneD286086Specdb::NmrOneD286087Specdb::NmrOneD286088Specdb::NmrOneD286089Specdb::NmrOneD286090Specdb::NmrOneD286091Specdb::NmrOneD286092Specdb::NmrOneD286093Specdb::NmrOneD286094Specdb::MsMs1327087Specdb::MsMs1327088Specdb::MsMs1327089Specdb::MsMs1441423Specdb::MsMs1441424Specdb::MsMs1441425Yurtsever 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(19:0/18:1(11Z)) + Glycerol 3-phosphate >2 PGP(19:0/18:1(11Z)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphatePW_R0055972 PGP(19:0/18:1(11Z)) + Water >2 PG(19:0/18:1(11Z)) + PhosphatePW_R005598