2.02015-09-08 19:32:52 -06002015-12-09 17:05:06 -0700ECMDB24444M2MDB006561PGP(12:0/12:0(3-OH))PGP(12:0/12:0(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(12:0/12:0(3-OH)), in particular, consists of one dodecanoyl chain to the C-1 atom, and one 3-hydroxydodecanoyl 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.C30H60O14P2706.744706.345830608[(2R)-3-({[(2R)-3-(dodecanoyloxy)-2-[(3-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid(2R)-3-{[(2R)-3-(dodecanoyloxy)-2-[(3-hydroxydodecanoyl)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)CCCCCCCCCInChI=1S/C30H60O14P2/c1-3-5-7-9-11-12-14-16-18-20-29(33)40-24-28(25-43-46(38,39)42-23-27(32)22-41-45(35,36)37)44-30(34)21-26(31)19-17-15-13-10-8-6-4-2/h26-28,31-32H,3-25H2,1-2H3,(H,38,39)(H2,35,36,37)/t26?,27-,28-/m1/s1HUWSGSFPGYJBAX-DXISBFFWSA-Nlogp3.54logs-4.57solubility1.89e-02 g/llogp6.03pka_strongest_acidic1.35pka_strongest_basic-2.8iupac[(2R)-3-({[(2R)-3-(dodecanoyloxy)-2-[(3-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acidaverage_mass706.744mono_mass706.345830608smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CC(O)CCCCCCCCCformulaC30H60O14P2inchiInChI=1S/C30H60O14P2/c1-3-5-7-9-11-12-14-16-18-20-29(33)40-24-28(25-43-46(38,39)42-23-27(32)22-41-45(35,36)37)44-30(34)21-26(31)19-17-15-13-10-8-6-4-2/h26-28,31-32H,3-25H2,1-2H3,(H,38,39)(H2,35,36,37)/t26?,27-,28-/m1/s1inchikeyHUWSGSFPGYJBAX-DXISBFFWSA-Npolar_surface_area215.58refractivity170.89polarizability77.12rotatable_bond_count34acceptor_count9donor_count5physiological_charge-3formal_charge0phospholipid biosynthesis (CL(12:0(3-OH)/12:0(3-OH)/12:0/12:0))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.
PW001915MetabolicSpecdb::CMs1085718Specdb::MsMs1324429Specdb::MsMs1324430Specdb::MsMs1324431Specdb::MsMs1438795Specdb::MsMs1438796Specdb::MsMs1438797Yurtsever 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(12:0/12:0(3-OH)) + Water >2 PG(12:0/12:0(3-OH)) + PhosphatePW_R005763