2.02012-07-30 14:55:10 -06002015-12-09 17:01:33 -0700ECMDB21274M2MDB001681PGP(18:1(11Z)/18:1(11Z))PGP(18:1(11Z)/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(18:1(11Z)/18:1(11Z)), in particular, consists of two 11Z-octadecenoyl chains at positions C-1 and C-2. 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.1,2-di(11Z-octadecenoyl)-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)1,2-Di(11Z-octadecenoyl)-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphoric acid)1,2-divaccenoyl-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)1,2-Divaccenoyl-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphoric acid)3-sn-Phosphatidyl-1'-sn-glycerol 3'-phosphate3-Sn-phosphatidyl-1'-sn-glycerol 3'-phosphorate3-Sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acidPGP(18:1/18:1)PGP(18:1n7/18:1n7)PGP(18:1w7/18:1w7)PGP(36:2)C42H80O13P2855.037854.507416632[(2R)-3-({[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid(2R)-3-{[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCCInChI=1S/C42H80O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(44)51-37-40(38-54-57(49,50)53-36-39(43)35-52-56(46,47)48)55-42(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,39-40,43H,3-12,17-38H2,1-2H3,(H,49,50)(H2,46,47,48)/b15-13-,16-14-/t39-,40-/m1/s1JUWFWNRVCXDDFB-ZAQZKMIBSA-NSolidMembranelogp7.47logs-6.15solubility6.04e-04 g/llogp11.87pka_strongest_acidic1.35pka_strongest_basic-3.4iupac[(2R)-3-({[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acidaverage_mass855.037mono_mass854.507416632smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCCformulaC42H80O13P2inchiInChI=1S/C42H80O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(44)51-37-40(38-54-57(49,50)53-36-39(43)35-52-56(46,47)48)55-42(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,39-40,43H,3-12,17-38H2,1-2H3,(H,49,50)(H2,46,47,48)/b15-13-,16-14-/t39-,40-/m1/s1inchikeyJUWFWNRVCXDDFB-ZAQZKMIBSA-Npolar_surface_area195.35refractivity226.82polarizability98.22rotatable_bond_count44acceptor_count8donor_count4physiological_charge-3formal_charge0phospholipid biosynthesis (CL(18:1(11Z)/19:0/18:1(11Z)/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.
PW001980Metabolicphospholipid 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.
PW001987MetabolicSpecdb::NmrOneD341688Specdb::NmrOneD341689Specdb::NmrOneD341690Specdb::NmrOneD341691Specdb::NmrOneD341692Specdb::NmrOneD341693Specdb::NmrOneD341694Specdb::NmrOneD341695Specdb::NmrOneD341696Specdb::NmrOneD341697Specdb::NmrOneD341698Specdb::NmrOneD341699Specdb::NmrOneD341700Specdb::NmrOneD341701Specdb::NmrOneD341702Specdb::NmrOneD341703Specdb::NmrOneD341704Specdb::NmrOneD341705Specdb::NmrOneD341706Specdb::NmrOneD341707Specdb::MsMs1233316Specdb::MsMs1233317Specdb::MsMs1233318Specdb::MsMs1348825Specdb::MsMs1348826Specdb::MsMs1348827HMDB13520Yurtsever 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.xmlLipid A export ATP-binding/permease protein msbAP60752MSBA_ECOLImsbAhttp://ecmdb.ca/proteins/P60752.xmlLipid A export ATP-binding/permease protein msbAP60752MSBA_ECOLImsbAhttp://ecmdb.ca/proteins/P60752.xmlWater + PGP(18:1(11Z)/18:1(11Z)) > PG(18:1(11Z)/18:1(11Z)) + PhosphateAdenosine triphosphate + Water + PGP(18:1(11Z)/18:1(11Z)) > ADP + Hydrogen ion + Phosphate + PGP(18:1(11Z)/18:1(11Z))Adenosine triphosphate + Water + PGP(18:1(11Z)/18:1(11Z)) > ADP + Hydrogen ion + Phosphate + PGP(18:1(11Z)/18:1(11Z))CDP-1,2-dioctadec-11-enoylglycerol + Glycerol 3-phosphate > Cytidine monophosphate + Hydrogen ion + PGP(18:1(11Z)/18:1(11Z))2 CDP-DG(18:1(9Z)/18:1(11Z)) + Glycerol 3-phosphate >2 PGP(18:1(11Z)/18:1(11Z)) + Cytidine monophosphate + Hydrogen ionPW_R0058642 PGP(18:1(11Z)/18:1(11Z)) + Water >2 PG(18:1(11Z)/18:1(11Z)) + PhosphatePW_R0058562 PGP(18:1(11Z)/18:1(11Z)) + Water >2 PG(18:1(11Z)/18:1(9Z)) + PhosphatePW_R0058572 PGP(18:1(11Z)/18:1(11Z)) + Water >2 PG(18:1(9Z)/18:1(11Z)) + PhosphatePW_R005860