2.02015-09-08 19:01:25 -06002015-12-09 17:04:12 -0700ECMDB24315M2MDB006432PGP(19:0/14:0)PGP(19:0/14:0) 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(19:0/14:0), in particular, consists of one nonadecanoyl chain to the C-1 atom, and one tetradecanoyl 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.C39H78O13P2816.988816.491766568[(2R)-2-hydroxy-3-({hydroxy[(2R)-3-(nonadecanoyloxy)-2-(tetradecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphonic acid(2R)-2-hydroxy-3-{[hydroxy((2R)-3-(nonadecanoyloxy)-2-(tetradecanoyloxy)propoxy)phosphoryl]oxy}propoxyphosphonic acid[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCInChI=1S/C39H78O13P2/c1-3-5-7-9-11-13-15-16-17-18-19-21-22-24-26-28-30-38(41)48-34-37(35-51-54(46,47)50-33-36(40)32-49-53(43,44)45)52-39(42)31-29-27-25-23-20-14-12-10-8-6-4-2/h36-37,40H,3-35H2,1-2H3,(H,46,47)(H2,43,44,45)/t36-,37-/m1/s1WLDCWECGXYOYIO-FZNHDDJXSA-Nlogp6.82logs-6.04solubility7.38e-04 g/llogp11.26pka_strongest_acidic1.35pka_strongest_basic-3.4iupac[(2R)-2-hydroxy-3-({hydroxy[(2R)-3-(nonadecanoyloxy)-2-(tetradecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphonic acidaverage_mass816.988mono_mass816.491766568smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCformulaC39H78O13P2inchiInChI=1S/C39H78O13P2/c1-3-5-7-9-11-13-15-16-17-18-19-21-22-24-26-28-30-38(41)48-34-37(35-51-54(46,47)50-33-36(40)32-49-53(43,44)45)52-39(42)31-29-27-25-23-20-14-12-10-8-6-4-2/h36-37,40H,3-35H2,1-2H3,(H,46,47)(H2,43,44,45)/t36-,37-/m1/s1inchikeyWLDCWECGXYOYIO-FZNHDDJXSA-Npolar_surface_area195.35refractivity210.78polarizability95.5rotatable_bond_count43acceptor_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.
PW001983MetabolicSpecdb::CMs1088057Specdb::NmrOneD254968Specdb::NmrOneD254969Specdb::NmrOneD254970Specdb::NmrOneD254971Specdb::NmrOneD254972Specdb::NmrOneD254973Specdb::NmrOneD254974Specdb::NmrOneD254975Specdb::NmrOneD254976Specdb::NmrOneD254977Specdb::NmrOneD254978Specdb::NmrOneD254979Specdb::NmrOneD254980Specdb::NmrOneD254981Specdb::NmrOneD254982Specdb::NmrOneD254983Specdb::NmrOneD254984Specdb::NmrOneD254985Specdb::NmrOneD254986Specdb::NmrOneD254987Specdb::MsMs1244824Specdb::MsMs1244825Specdb::MsMs1244826Specdb::MsMs1360192Specdb::MsMs1360193Specdb::MsMs1360194Yurtsever 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.xmlPhosphatidylglycerophosphatase AP18200PGPA_ECOLIpgpAhttp://ecmdb.ca/proteins/P18200.xml2 PGP(19:0/14:0) + Water >2 PG(19:0/14:0) + PhosphatePW_R005771