2.02015-09-08 19:34:37 -06002015-12-09 17:19:54 -0700ECMDB24480M2MDB006597PGP(15:0cyclo/19:0cycv8c)PGP(15:0cyclo/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(15:0cyclo/19:0cycv8c), in particular, consists of one cis-9,10-Methylenetetradecanoic acid 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.C40H76O13P2826.983826.476116503[(2R)-3-({[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid(2R)-3-{[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCC)OC(=O)CCCCCCCCCC1CC1CCCCCCInChI=1S/C40H76O13P2/c1-3-5-7-16-22-35-28-36(35)24-17-12-9-8-10-14-20-26-40(43)53-38(32-52-55(47,48)51-30-37(41)29-50-54(44,45)46)31-49-39(42)25-19-15-11-13-18-23-34-27-33(34)21-6-4-2/h33-38,41H,3-32H2,1-2H3,(H,47,48)(H2,44,45,46)/t33?,34?,35?,36?,37-,38-/m1/s1KPBARYCBNDDAHF-RTDSVYOCSA-Nlogp6.59logs-6.04solubility7.50e-04 g/llogp10.14pka_strongest_acidic1.35pka_strongest_basic-3.4iupac[(2R)-3-({[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acidaverage_mass826.983mono_mass826.476116503smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCC)OC(=O)CCCCCCCCCC1CC1CCCCCCformulaC40H76O13P2inchiInChI=1S/C40H76O13P2/c1-3-5-7-16-22-35-28-36(35)24-17-12-9-8-10-14-20-26-40(43)53-38(32-52-55(47,48)51-30-37(41)29-50-54(44,45)46)31-49-39(42)25-19-15-11-13-18-23-34-27-33(34)21-6-4-2/h33-38,41H,3-32H2,1-2H3,(H,47,48)(H2,44,45,46)/t33?,34?,35?,36?,37-,38-/m1/s1inchikeyKPBARYCBNDDAHF-RTDSVYOCSA-Npolar_surface_area195.35refractivity211.57polarizability94.49rotatable_bond_count40acceptor_count8donor_count4physiological_charge-3formal_charge0phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/15:0cyclo/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."PW001065MetabolicSpecdb::CMs1089397Specdb::EiMs4818Specdb::NmrOneD289315Specdb::NmrOneD289316Specdb::NmrOneD289317Specdb::NmrOneD289318Specdb::NmrOneD289319Specdb::NmrOneD289320Specdb::NmrOneD289321Specdb::NmrOneD289322Specdb::NmrOneD289323Specdb::NmrOneD289324Specdb::NmrOneD289325Specdb::NmrOneD289326Specdb::NmrOneD289327Specdb::NmrOneD289328Specdb::NmrOneD289329Specdb::NmrOneD289330Specdb::NmrOneD289331Specdb::NmrOneD289332Specdb::NmrOneD289333Specdb::NmrOneD289334Specdb::MsMs1288237Specdb::MsMs1288238Specdb::MsMs1288239Specdb::MsMs1403008Specdb::MsMs1403009Specdb::MsMs1403010Yurtsever 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(15:0cyclo/19:0cycv8c) + Water >2 PG(15:0cyclo/19:0cycv8c) + PhosphatePW_R005779