2.02015-09-08 19:39:57 -06002016-09-13 16:36:11 -0600ECMDB24543M2MDB006660PGP(19:iso/18:1(9Z))PGP(19:iso/18:1(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:iso/18:1(9Z)), in particular, consists of one 17-methylocatdecanoyl chain to the C-1 atom, and one 9Z-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[(2S)-2-hydroxy-3-({hydroxy[(2R)-3-[(17-methyloctadecanoyl)oxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid(2S)-2-hydroxy-3-{[hydroxy((2R)-3-[(17-methyloctadecanoyl)oxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy)phosphoryl]oxy}propoxyphosphonic acid[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCCInChI=1S/C43H84O13P2/c1-4-5-6-7-8-9-10-11-12-15-19-22-25-28-31-34-43(46)56-41(38-55-58(50,51)54-36-40(44)35-53-57(47,48)49)37-52-42(45)33-30-27-24-21-18-16-13-14-17-20-23-26-29-32-39(2)3/h11-12,39-41,44H,4-10,13-38H2,1-3H3,(H,50,51)(H2,47,48,49)/b12-11-/t40-,41+/m0/s1XUGRLCBKDWAUDQ-UWSJFRPISA-Nlogp7.47logs-6.29solubility4.49e-04 g/llogp12.52pka_strongest_acidic1.35pka_strongest_basic-3.4iupac[(2S)-2-hydroxy-3-({hydroxy[(2R)-3-[(17-methyloctadecanoyl)oxy]-2-[(9Z)-octadec-9-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)CCCCCCCCCCCCCCCC(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCCformulaC43H84O13P2inchiInChI=1S/C43H84O13P2/c1-4-5-6-7-8-9-10-11-12-15-19-22-25-28-31-34-43(46)56-41(38-55-58(50,51)54-36-40(44)35-53-57(47,48)49)37-52-42(45)33-30-27-24-21-18-16-13-14-17-20-23-26-29-32-39(2)3/h11-12,39-41,44H,4-10,13-38H2,1-3H3,(H,50,51)(H2,47,48,49)/b12-11-/t40-,41+/m0/s1inchikeyXUGRLCBKDWAUDQ-UWSJFRPISA-Npolar_surface_area195.35refractivity230.25polarizability102.27rotatable_bond_count45acceptor_count8donor_count4physiological_charge-3formal_charge0phospholipid biosynthesis (CL(19:0cycv8c/16:0/19:0cycv8c/18:1(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.PW001373MetabolicSpecdb::NmrOneD308031Specdb::NmrOneD308032Specdb::NmrOneD308033Specdb::NmrOneD308034Specdb::NmrOneD308035Specdb::NmrOneD308036Specdb::NmrOneD308037Specdb::NmrOneD308038Specdb::NmrOneD308039Specdb::NmrOneD308040Specdb::NmrOneD308041Specdb::NmrOneD308042Specdb::NmrOneD308043Specdb::NmrOneD308044Specdb::NmrOneD308045Specdb::NmrOneD308046Specdb::NmrOneD308047Specdb::NmrOneD308048Specdb::NmrOneD308049Specdb::NmrOneD308050Specdb::MsMs26558Specdb::MsMs26559Specdb::MsMs26560Specdb::MsMs33116Specdb::MsMs33117Specdb::MsMs33118Yurtsever 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:iso/18:1(9Z)) + Water >2 PG(19:iso/18:1(9Z)) + PhosphatePW_R005759