2.02015-09-08 19:31:36 -06002015-12-09 17:18:05 -0700ECMDB24417M2MDB006534PGP(10:0(3-OH)/15:0)PGP(10:0(3-OH)/15:0) 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(10:0(3-OH)/15:0), in particular, consists of one 3-hydroxydecanoyl chain to the C-1 atom, and one pentadecanoyl 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.C31H62O14P2720.771720.361480672[(2R)-2-hydroxy-3-({hydroxy[(2R)-3-[(3-hydroxydecanoyl)oxy]-2-(pentadecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphonic acid(2R)-2-hydroxy-3-{[hydroxy((2R)-3-[(3-hydroxydecanoyl)oxy]-2-(pentadecanoyloxy)propoxy)phosphoryl]oxy}propoxyphosphonic acid[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCC)OC(=O)CCCCCCCCCCCCCCInChI=1S/C31H62O14P2/c1-3-5-7-9-10-11-12-13-14-15-17-19-21-30(34)45-29(25-41-31(35)22-27(32)20-18-16-8-6-4-2)26-44-47(39,40)43-24-28(33)23-42-46(36,37)38/h27-29,32-33H,3-26H2,1-2H3,(H,39,40)(H2,36,37,38)/t27?,28-,29-/m1/s1ZWEKOQKPFOJXST-NPQGXCPKSA-Nlogp3.89logs-4.82solubility1.08e-02 g/llogp6.47pka_strongest_acidic1.35pka_strongest_basic-2.8iupac[(2R)-2-hydroxy-3-({hydroxy[(2R)-3-[(3-hydroxydecanoyl)oxy]-2-(pentadecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphonic acidaverage_mass720.771mono_mass720.361480672smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCC)OC(=O)CCCCCCCCCCCCCCformulaC31H62O14P2inchiInChI=1S/C31H62O14P2/c1-3-5-7-9-10-11-12-13-14-15-17-19-21-30(34)45-29(25-41-31(35)22-27(32)20-18-16-8-6-4-2)26-44-47(39,40)43-24-28(33)23-42-46(36,37)38/h27-29,32-33H,3-26H2,1-2H3,(H,39,40)(H2,36,37,38)/t27?,28-,29-/m1/s1inchikeyZWEKOQKPFOJXST-NPQGXCPKSA-Npolar_surface_area215.58refractivity175.49polarizability78.38rotatable_bond_count35acceptor_count9donor_count5physiological_charge-3formal_charge0phospholipid biosynthesis (CL(15:0/10:0(3-OH)/15:0/10:0(3-OH)))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.
PW001945MetabolicSpecdb::CMs1086379Specdb::NmrOneD329842Specdb::NmrOneD329843Specdb::NmrOneD329844Specdb::NmrOneD329845Specdb::NmrOneD329846Specdb::NmrOneD329847Specdb::NmrOneD329848Specdb::NmrOneD329849Specdb::NmrOneD329850Specdb::NmrOneD329851Specdb::NmrOneD329852Specdb::NmrOneD329853Specdb::NmrOneD329854Specdb::NmrOneD329855Specdb::NmrOneD329856Specdb::NmrOneD329857Specdb::NmrOneD329858Specdb::NmrOneD329859Specdb::NmrOneD329860Specdb::NmrOneD329861Specdb::MsMs1277290Specdb::MsMs1277291Specdb::MsMs1277292Specdb::MsMs1392208Specdb::MsMs1392209Specdb::MsMs1392210Yurtsever 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(10:0(3-OH)/15:0) + Water >2 PG(10:0(3-OH)/15:0) + PhosphatePW_R005851