2.02015-09-08 19:31:59 -06002015-12-09 17:04:51 -0700ECMDB24425M2MDB006542PGP(10:0/10:0(3-OH))PGP(10:0/10:0(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(10:0/10:0(3-OH)), in particular, consists of one decanoyl 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.C26H52O14P2650.636650.28323035[(2R)-3-({[(2R)-3-(decanoyloxy)-2-[(3-hydroxydecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid(2R)-3-{[(2R)-3-(decanoyloxy)-2-[(3-hydroxydecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC)OC(=O)CC(O)CCCCCCCInChI=1S/C26H52O14P2/c1-3-5-7-9-10-12-14-16-25(29)36-20-24(40-26(30)17-22(27)15-13-11-8-6-4-2)21-39-42(34,35)38-19-23(28)18-37-41(31,32)33/h22-24,27-28H,3-21H2,1-2H3,(H,34,35)(H2,31,32,33)/t22?,23-,24-/m1/s1HVCXGYDISAURMK-HEYJASKDSA-Nlogp2.38logs-3.58solubility1.72e-01 g/llogp4.25pka_strongest_acidic1.35pka_strongest_basic-2.8iupac[(2R)-3-({[(2R)-3-(decanoyloxy)-2-[(3-hydroxydecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acidaverage_mass650.636mono_mass650.28323035smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC)OC(=O)CC(O)CCCCCCCformulaC26H52O14P2inchiInChI=1S/C26H52O14P2/c1-3-5-7-9-10-12-14-16-25(29)36-20-24(40-26(30)17-22(27)15-13-11-8-6-4-2)21-39-42(34,35)38-19-23(28)18-37-41(31,32)33/h22-24,27-28H,3-21H2,1-2H3,(H,34,35)(H2,31,32,33)/t22?,23-,24-/m1/s1inchikeyHVCXGYDISAURMK-HEYJASKDSA-Npolar_surface_area215.58refractivity152.49polarizability68.48rotatable_bond_count30acceptor_count9donor_count5physiological_charge-3formal_charge0phospholipid biosynthesis (CL(10:0/10:0(3-OH)/10:0/10:0(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.PW001910MetabolicSpecdb::CMs1085554Specdb::NmrOneD248548Specdb::NmrOneD248549Specdb::NmrOneD248550Specdb::NmrOneD248551Specdb::NmrOneD248552Specdb::NmrOneD248553Specdb::NmrOneD248554Specdb::NmrOneD248555Specdb::NmrOneD248556Specdb::NmrOneD248557Specdb::NmrOneD248558Specdb::NmrOneD248559Specdb::NmrOneD248560Specdb::NmrOneD248561Specdb::NmrOneD248562Specdb::NmrOneD248563Specdb::NmrOneD248564Specdb::NmrOneD248565Specdb::NmrOneD248566Specdb::NmrOneD248567Specdb::MsMs1270018Specdb::MsMs1270019Specdb::MsMs1270020Specdb::MsMs1385035Specdb::MsMs1385036Specdb::MsMs1385037Yurtsever 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(10:0/10:0(3-OH)) + Glycerol 3-phosphate >2 PGP(10:0/10:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphatePW_R0053242 PGP(10:0/10:0(3-OH)) + Water >2 PG(10:0/10:0(3-OH)) + PhosphatePW_R005325