2.02015-09-08 19:32:10 -06002015-12-09 17:18:14 -0700ECMDB24429M2MDB006546PGP(12:0(3-OH)/10:0(3-OH))PGP(12:0(3-OH)/10:0(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(3-OH)/10:0(3-OH)), in particular, consists of one 3-hydroxydodecanoyl chain to the C-1 atom, and one 3-hydroxydecanoyl 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.C28H56O15P2694.689694.309445099[(2R)-2-hydroxy-3-({hydroxy[(2R)-2-[(3-hydroxydecanoyl)oxy]-3-[(3-hydroxydodecanoyl)oxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid(2R)-2-hydroxy-3-{[hydroxy((2R)-2-[(3-hydroxydecanoyl)oxy]-3-[(3-hydroxydodecanoyl)oxy]propoxy)phosphoryl]oxy}propoxyphosphonic acid[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCC)OC(=O)CC(O)CCCCCCCInChI=1S/C28H56O15P2/c1-3-5-7-9-10-12-14-15-23(29)17-27(32)39-21-26(43-28(33)18-24(30)16-13-11-8-6-4-2)22-42-45(37,38)41-20-25(31)19-40-44(34,35)36/h23-26,29-31H,3-22H2,1-2H3,(H,37,38)(H2,34,35,36)/t23?,24?,25-,26-/m1/s1UBJFKYNBHSLUNY-CVQXOBEKSA-Nlogp2.15logs-3.65solubility1.57e-01 g/llogp3.91pka_strongest_acidic1.35pka_strongest_basic-2.8iupac[(2R)-2-hydroxy-3-({hydroxy[(2R)-2-[(3-hydroxydecanoyl)oxy]-3-[(3-hydroxydodecanoyl)oxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acidaverage_mass694.689mono_mass694.309445099smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCC)OC(=O)CC(O)CCCCCCCformulaC28H56O15P2inchiInChI=1S/C28H56O15P2/c1-3-5-7-9-10-12-14-15-23(29)17-27(32)39-21-26(43-28(33)18-24(30)16-13-11-8-6-4-2)22-42-45(37,38)41-20-25(31)19-40-44(34,35)36/h23-26,29-31H,3-22H2,1-2H3,(H,37,38)(H2,34,35,36)/t23?,24?,25-,26-/m1/s1inchikeyUBJFKYNBHSLUNY-CVQXOBEKSA-Npolar_surface_area235.81refractivity163.2polarizability73.15rotatable_bond_count32acceptor_count10donor_count6physiological_charge-3formal_charge0phospholipid biosynthesis (CL(12:0(3-OH)/10:0(3-OH)/12:0(3-OH)/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.
PW001913MetabolicSpecdb::CMs1084798Specdb::MsMs1252438Specdb::MsMs1252439Specdb::MsMs1252440Specdb::MsMs1367686Specdb::MsMs1367687Specdb::MsMs1367688Yurtsever 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(3-OH)/10:0(3-OH)) + Glycerol 3-phosphate >2 PGP(12:0(3-OH)/10:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphatePW_R0053392 PGP(12:0(3-OH)/10:0(3-OH)) + Water >2 PG(12:0(3-OH)/10:0(3-OH)) + PhosphatePW_R005340