2.02015-09-08 19:00:46 -06002015-12-09 17:03:44 -0700ECMDB24299M2MDB006416PGP(17:0/16:0)PGP(17:0/16:0) 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(17:0/16:0), in particular, consists of one heptadecanoyl chain to the C-1 atom, and one hexadecanoyl 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)-3-({[(2R)-3-(heptadecanoyloxy)-2-(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid(2R)-3-{[(2R)-3-(heptadecanoyloxy)-2-(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCInChI=1S/C39H78O13P2/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-38(41)48-34-37(35-51-54(46,47)50-33-36(40)32-49-53(43,44)45)52-39(42)31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h36-37,40H,3-35H2,1-2H3,(H,46,47)(H2,43,44,45)/t36-,37-/m1/s1WJWYSHXVCBHPJZ-FZNHDDJXSA-Nlogp6.81logs-6.04solubility7.44e-04 g/llogp11.26pka_strongest_acidic1.35pka_strongest_basic-3.4iupac[(2R)-3-({[(2R)-3-(heptadecanoyloxy)-2-(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acidaverage_mass816.988mono_mass816.491766568smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCformulaC39H78O13P2inchiInChI=1S/C39H78O13P2/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-38(41)48-34-37(35-51-54(46,47)50-33-36(40)32-49-53(43,44)45)52-39(42)31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h36-37,40H,3-35H2,1-2H3,(H,46,47)(H2,43,44,45)/t36-,37-/m1/s1inchikeyWJWYSHXVCBHPJZ-FZNHDDJXSA-Npolar_surface_area195.35refractivity210.78polarizability95.39rotatable_bond_count43acceptor_count8donor_count4physiological_charge-3formal_charge0phospholipid biosynthesis (CL(17:0/16:1(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.
PW001964MetabolicSpecdb::CMs1084630Specdb::NmrOneD320971Specdb::NmrOneD320972Specdb::NmrOneD320973Specdb::NmrOneD320974Specdb::NmrOneD320975Specdb::NmrOneD320976Specdb::NmrOneD320977Specdb::NmrOneD320978Specdb::NmrOneD320979Specdb::NmrOneD320980Specdb::NmrOneD320981Specdb::NmrOneD320982Specdb::NmrOneD320983Specdb::NmrOneD320984Specdb::NmrOneD320985Specdb::NmrOneD320986Specdb::NmrOneD320987Specdb::NmrOneD320988Specdb::NmrOneD320989Specdb::NmrOneD320990Specdb::MsMs1314703Specdb::MsMs1314704Specdb::MsMs1314705Specdb::MsMs1429186Specdb::MsMs1429187Specdb::MsMs1429188Yurtsever 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(17:0/16:0) + Water >2 PG(17:0/16:0) + PhosphatePW_R005781