2.02015-09-08 19:35:54 -06002015-12-09 17:21:01 -0700ECMDB24504M2MDB006621PGP(17:0cycw7c/19:0cycv8c)PGP(17:0cycw7c/19:0cycv8c) 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(17:0cycw7c/19:0cycv8c), in particular, consists of one heptadec-9-10-cyclo-anoyl chain to the C-1 atom, and one heptadec-11-12-cyclo-anoyl 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.C42H80O13P2855.037854.507416632[(2R)-3-({[(2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid(2R)-3-{[(2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCCCCC1CC1CCCCCCInChI=1S/C42H80O13P2/c1-3-5-7-17-23-35-29-37(35)25-19-13-10-9-11-15-22-28-42(45)55-40(34-54-57(49,50)53-32-39(43)31-52-56(46,47)48)33-51-41(44)27-21-16-12-14-20-26-38-30-36(38)24-18-8-6-4-2/h35-40,43H,3-34H2,1-2H3,(H,49,50)(H2,46,47,48)/t35?,36?,37?,38?,39-,40-/m1/s1IOQCYOCDLMYJIX-WRGXHSNHSA-Nlogp7.07logs-6.14solubility6.14e-04 g/llogp11.03pka_strongest_acidic1.35pka_strongest_basic-3.4iupac[(2R)-3-({[(2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}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)CCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCCCCC1CC1CCCCCCformulaC42H80O13P2inchiInChI=1S/C42H80O13P2/c1-3-5-7-17-23-35-29-37(35)25-19-13-10-9-11-15-22-28-42(45)55-40(34-54-57(49,50)53-32-39(43)31-52-56(46,47)48)33-51-41(44)27-21-16-12-14-20-26-38-30-36(38)24-18-8-6-4-2/h35-40,43H,3-34H2,1-2H3,(H,49,50)(H2,46,47,48)/t35?,36?,37?,38?,39-,40-/m1/s1inchikeyIOQCYOCDLMYJIX-WRGXHSNHSA-Npolar_surface_area195.35refractivity220.77polarizability98.65rotatable_bond_count42acceptor_count8donor_count4physiological_charge-3formal_charge0phospholipid biosynthesis (CL(19:0cycv8c/17:0cycw7c/17:0cycw7c/19:0cycv8c))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.PW001406MetabolicSpecdb::MsMs1301854Specdb::MsMs1301855Specdb::MsMs1301856Specdb::MsMs1416439Specdb::MsMs1416440Specdb::MsMs1416441Yurtsever 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(17:0cycw7c/19:0cycv8c) + Water >2 PG(17:0cycw7c/19:0cycv8c) + PhosphatePW_R005792