2.02015-09-08 19:01:31 -06002015-12-09 17:04:16 -0700ECMDB24317M2MDB006434PGP(19:0/16:1(9Z))PGP(19:0/16:1(9Z)) 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(19:0/16:1(9Z)), in particular, consists of one nonadecanoyl chain to the C-1 atom, and one 9Z-hexadecenoyl 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.C41H80O13P2843.026842.507416632[(2R)-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(nonadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid(2R)-3-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(nonadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCInChI=1S/C41H80O13P2/c1-3-5-7-9-11-13-15-17-18-19-21-22-24-26-28-30-32-40(43)50-36-39(37-53-56(48,49)52-35-38(42)34-51-55(45,46)47)54-41(44)33-31-29-27-25-23-20-16-14-12-10-8-6-4-2/h14,16,38-39,42H,3-13,15,17-37H2,1-2H3,(H,48,49)(H2,45,46,47)/b16-14-/t38-,39-/m1/s1BYWHNNWGULJPLT-GYNJEZAQSA-Nlogp7.31logs-6.14solubility6.07e-04 g/llogp11.79pka_strongest_acidic1.35pka_strongest_basic-3.4iupac[(2R)-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(nonadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acidaverage_mass843.026mono_mass842.507416632smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCformulaC41H80O13P2inchiInChI=1S/C41H80O13P2/c1-3-5-7-9-11-13-15-17-18-19-21-22-24-26-28-30-32-40(43)50-36-39(37-53-56(48,49)52-35-38(42)34-51-55(45,46)47)54-41(44)33-31-29-27-25-23-20-16-14-12-10-8-6-4-2/h14,16,38-39,42H,3-13,15,17-37H2,1-2H3,(H,48,49)(H2,45,46,47)/b16-14-/t38-,39-/m1/s1inchikeyBYWHNNWGULJPLT-GYNJEZAQSA-Npolar_surface_area195.35refractivity221.1polarizability98.33rotatable_bond_count44acceptor_count8donor_count4physiological_charge-3formal_charge0phospholipid biosynthesis (CL(19:0/16:1(9Z)/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.
PW001983Metabolicphospholipid biosynthesis (CL(19:0/16:1(9Z)/16:0/16:0))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.
PW001984Metabolicphospholipid biosynthesis (CL(19:0/16:1(9Z)/19:0/16:1(9Z)))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.
PW001985MetabolicSpecdb::NmrOneD247788Specdb::NmrOneD247789Specdb::NmrOneD247790Specdb::NmrOneD247791Specdb::NmrOneD247792Specdb::NmrOneD247793Specdb::NmrOneD247794Specdb::NmrOneD247795Specdb::NmrOneD247796Specdb::NmrOneD247797Specdb::NmrOneD247798Specdb::NmrOneD247799Specdb::NmrOneD247800Specdb::NmrOneD247801Specdb::NmrOneD247802Specdb::NmrOneD247803Specdb::NmrOneD247804Specdb::NmrOneD247805Specdb::NmrOneD247806Specdb::NmrOneD247807Specdb::MsMs1326103Specdb::MsMs1326104Specdb::MsMs1326105Specdb::MsMs1440451Specdb::MsMs1440452Specdb::MsMs1440453Yurtsever 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(19:0/16:1(9Z)) + Glycerol 3-phosphate >2 PGP(19:0/16:1(9Z)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphatePW_R0055912 PGP(19:0/16:1(9Z)) + Water >2 PG(19:0/16:1(9Z)) + PhosphatePW_R005592