2.02015-09-08 19:32:55 -06002015-12-09 17:05:10 -0700ECMDB24445M2MDB006562PGP(12:0/14:0(3-OH))PGP(12:0/14:0(3-OH)) 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(12:0/14:0(3-OH)), in particular, consists of one dodecanoyl chain to the C-1 atom, and one 3-hydroxytetradecanoyl 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.C32H64O14P2734.798734.377130737[(2R)-3-({[(2R)-3-(dodecanoyloxy)-2-[(3-hydroxytetradecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid(2R)-3-{[(2R)-3-(dodecanoyloxy)-2-[(3-hydroxytetradecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CC(O)CCCCCCCCCCCInChI=1S/C32H64O14P2/c1-3-5-7-9-11-13-15-17-19-21-28(33)23-32(36)46-30(26-42-31(35)22-20-18-16-14-12-10-8-6-4-2)27-45-48(40,41)44-25-29(34)24-43-47(37,38)39/h28-30,33-34H,3-27H2,1-2H3,(H,40,41)(H2,37,38,39)/t28?,29-,30-/m1/s1QEOSSPVRSXIFAP-GVKMRLRKSA-Nlogp4.16logs-4.94solubility8.45e-03 g/llogp6.92pka_strongest_acidic1.35pka_strongest_basic-2.8iupac[(2R)-3-({[(2R)-3-(dodecanoyloxy)-2-[(3-hydroxytetradecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acidaverage_mass734.798mono_mass734.377130737smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CC(O)CCCCCCCCCCCformulaC32H64O14P2inchiInChI=1S/C32H64O14P2/c1-3-5-7-9-11-13-15-17-19-21-28(33)23-32(36)46-30(26-42-31(35)22-20-18-16-14-12-10-8-6-4-2)27-45-48(40,41)44-25-29(34)24-43-47(37,38)39/h28-30,33-34H,3-27H2,1-2H3,(H,40,41)(H2,37,38,39)/t28?,29-,30-/m1/s1inchikeyQEOSSPVRSXIFAP-GVKMRLRKSA-Npolar_surface_area215.58refractivity180.09polarizability81.38rotatable_bond_count36acceptor_count9donor_count5physiological_charge-3formal_charge0phospholipid biosynthesis (CL(12:0/14:0(3-OH)/12:0/14:0(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.
PW001931MetabolicSpecdb::CMs1086505Specdb::NmrOneD275798Specdb::NmrOneD275799Specdb::NmrOneD275800Specdb::NmrOneD275801Specdb::NmrOneD275802Specdb::NmrOneD275803Specdb::NmrOneD275804Specdb::NmrOneD275805Specdb::NmrOneD275806Specdb::NmrOneD275807Specdb::NmrOneD275808Specdb::NmrOneD275809Specdb::NmrOneD275810Specdb::NmrOneD275811Specdb::NmrOneD275812Specdb::NmrOneD275813Specdb::NmrOneD275814Specdb::NmrOneD275815Specdb::NmrOneD275816Specdb::NmrOneD275817Specdb::MsMs1266919Specdb::MsMs1266920Specdb::MsMs1266921Specdb::MsMs1381969Specdb::MsMs1381970Specdb::MsMs1381971Yurtsever 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.xmlCDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferaseP0ABF8PGSA_ECOLIpgsAhttp://ecmdb.ca/proteins/P0ABF8.xmlPhosphatidylglycerophosphatase AP18200PGPA_ECOLIpgpAhttp://ecmdb.ca/proteins/P18200.xml2 CDP-DG(12:0/14:0(3-OH)) + Glycerol 3-phosphate >2 PGP(12:0/14:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphatePW_R0054132 PGP(12:0/14:0(3-OH)) + Water >2 PG(12:0/14:0(3-OH)) + PhosphatePW_R005414