2.02012-10-24 09:54:52 -06002015-12-09 12:06:05 -0700ECMDB23640M2MDB004030PG(10:0(3-OH)/16:1(9Z))PG(10:0(3-OH)/16:1(9Z)) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(10:0(3-OH)/16:1(9Z)), in particular, consists of one 3-hydroxydecanoyl chain to the C-1 atom, and one 9Z-hexadecenoyl to the C-2 atom. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes.1-3-hydroxydecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phospho-(1'-glycerol)1-3-hydroxydecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphoglycerol1-3-hydroxydecanoyl-2-palmitoleoyl-sn-glycero-3-phosphoglycerol1-NULL-2-(9Z-hexadecenoyl)-sn-glycero-3-phospho-(1'-glycerol)1-NULL-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphoglycerolGPG(10:0/16:1)GPG(26:1)PG(10:0/16:1)PG(26:1)Phosphatidylglycerol(10:0/16:1)Phosphatidylglycerol(26:1)C32H61O11P652.803652.395149782[(2S)-2,3-dihydroxypropoxy][(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(3-hydroxydecanoyl)oxy]propoxy]phosphinic acid(2S)-2,3-dihydroxypropoxy((2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(3-hydroxydecanoyl)oxy]propoxy)phosphinic acid[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CC(O)CCCCCCCInChI=1S/C32H61O11P/c1-3-5-7-9-10-11-12-13-14-15-16-18-20-22-31(36)40-26-30(27-42-44(38,39)41-25-29(35)24-33)43-32(37)23-28(34)21-19-17-8-6-4-2/h11-12,28-30,33-35H,3-10,13-27H2,1-2H3,(H,38,39)/b12-11-/t28?,29-,30+/m0/s1IMPXUTLHCUEPBX-MIJJTBKJSA-NSolidMembranelogp5.14logs-5.78solubility1.09e-03 g/llogp6.68pka_strongest_acidic1.89pka_strongest_basic-2.8iupac[(2S)-2,3-dihydroxypropoxy][(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(3-hydroxydecanoyl)oxy]propoxy]phosphinic acidaverage_mass652.803mono_mass652.395149782smiles[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CC(O)CCCCCCCformulaC32H61O11PinchiInChI=1S/C32H61O11P/c1-3-5-7-9-10-11-12-13-14-15-16-18-20-22-31(36)40-26-30(27-42-44(38,39)41-25-29(35)24-33)43-32(37)23-28(34)21-19-17-8-6-4-2/h11-12,28-30,33-35H,3-10,13-27H2,1-2H3,(H,38,39)/b12-11-/t28?,29-,30+/m0/s1inchikeyIMPXUTLHCUEPBX-MIJJTBKJSA-Npolar_surface_area169.05refractivity170.34polarizability73.89rotatable_bond_count33acceptor_count7donor_count4physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(10:0(3-OH)/16:1(9Z)/10:0(3-OH)/16:1(9Z)))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.
PW001903MetabolicSpecdb::CMs1084782Specdb::MsMs1294555Specdb::MsMs1294556Specdb::MsMs1294557Specdb::MsMs1409215Specdb::MsMs1409216Specdb::MsMs1409217Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510Yuan Y, Leeds JA, Meredith TC (2012). "Pseudomonas aeruginosa Directly Shunts β-Oxidation Degradation Intermediates into De Novo Fatty Acid Biosynthesis." J Bacteriol. 194(19):5185-9622753057Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.ALysophospholipase L2P07000PLDB_ECOLIpldBhttp://ecmdb.ca/proteins/P07000.xmlPhosphatidylglycerophosphatase BP0A924PGPB_ECOLIpgpBhttp://ecmdb.ca/proteins/P0A924.xmlPhosphatidylglycerophosphatase AP18200PGPA_ECOLIpgpAhttp://ecmdb.ca/proteins/P18200.xmlLipid A export ATP-binding/permease protein msbAP60752MSBA_ECOLImsbAhttp://ecmdb.ca/proteins/P60752.xmlProtein crcAP37001CRCA_ECOLIcrcAhttp://ecmdb.ca/proteins/P37001.xmlCardiolipin synthaseP0A6H8CLS_ECOLIclshttp://ecmdb.ca/proteins/P0A6H8.xmlPutative cardiolipin synthase ybhOP0AA84YBHO_ECOLIybhOhttp://ecmdb.ca/proteins/P0AA84.xmlProbable phospholipid ABC transporter-binding protein mlaBP64602MLAB_ECOLImlaBhttp://ecmdb.ca/proteins/P64602.xmlLipid A export ATP-binding/permease protein msbAP60752MSBA_ECOLImsbAhttp://ecmdb.ca/proteins/P60752.xmlProbable phospholipid ABC transporter-binding protein mlaDP64604MLAD_ECOLImlaDhttp://ecmdb.ca/proteins/P64604.xmlProbable phospholipid ABC transporter permease protein mlaEP64606MLAE_ECOLImlaEhttp://ecmdb.ca/proteins/P64606.xml2 PGP(10:0(3-OH)/16:1(9Z)) + Water >2 PG(10:0(3-OH)/16:1(9Z)) + PhosphatePW_R0053042 PG(10:0(3-OH)/16:1(9Z)) > Glycerol + CL(10:0(3-OH)/16:1(9Z)/10:0(3-OH)/16:1(9Z))PW_R005305