2.02012-05-31 14:57:12 -06002015-12-09 12:08:08 -0700ECMDB21068M2MDB001484PG(18:1(11Z)/19:0)PG(18:1(11Z)/19:0) 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(18:1(11Z)/19:0), in particular, consists of one 11Z-octadecenoyl chain to the C-1 atom, and one nonadecanoyl 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-(11Z-octadecenoyl)-2-nonadecanoyl-sn-glycero-3-phospho-(1'-glycerol)1-(11Z-octadecenoyl)-2-nonadecanoyl-sn-glycero-3-phosphoglycerol1-vaccenoyl-2--sn-glycero-3-phosphoglycerol1-vaccenoyl-2-nonadecanoyl-sn-glycero-3-phosphoglycerolGPG(18:1/19:0)GPG(37:1)PG(18:1/19:0)PG(37:1)Phosphatidylglycerol(18:1/19:0)Phosphatidylglycerol(37:1)C43H83O10P791.0869790.572385388[(2S)-2,3-dihydroxypropoxy][(2R)-3-(nonadecanoyloxy)-2-[(11Z)-octadec-11-enoyloxy]propoxy]phosphinic acid(2S)-2,3-dihydroxypropoxy((2R)-3-(nonadecanoyloxy)-2-[(11Z)-octadec-11-enoyloxy]propoxy)phosphinic acid[H]\C(CCCCCC)=C(/[H])CCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(O)COInChI=1S/C43H83O10P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-42(46)50-38-41(39-52-54(48,49)51-37-40(45)36-44)53-43(47)35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h14,16,40-41,44-45H,3-13,15,17-39H2,1-2H3,(H,48,49)/b16-14-/t40-,41+/m0/s1BGUZYINAHUNNTB-HLEWSJEYSA-NInner membraneMembraneOuter membranelogp8.75logs-7.05solubility6.98e-05 g/llogp12.8pka_strongest_acidic1.89pka_strongest_basic-3iupac[(2S)-2,3-dihydroxypropoxy][(2R)-3-(nonadecanoyloxy)-2-[(11Z)-octadec-11-enoyloxy]propoxy]phosphinic acidaverage_mass791.0869mono_mass790.572385388smiles[H]\C(CCCCCC)=C(/[H])CCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(O)COformulaC43H83O10PinchiInChI=1S/C43H83O10P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-42(46)50-38-41(39-52-54(48,49)51-37-40(45)36-44)53-43(47)35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h14,16,40-41,44-45H,3-13,15,17-39H2,1-2H3,(H,48,49)/b16-14-/t40-,41+/m0/s1inchikeyBGUZYINAHUNNTB-HLEWSJEYSA-Npolar_surface_area148.82refractivity219.43polarizability96.66rotatable_bond_count44acceptor_count6donor_count3physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(18:1(11Z)/19:0/18:1(11Z)/19:0))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.
PW001980Metabolicphospholipid biosynthesis IPHOSLIPSYN-PWYSpecdb::CMs1084714Specdb::NmrOneD292035Specdb::NmrOneD292036Specdb::NmrOneD292037Specdb::NmrOneD292038Specdb::NmrOneD292039Specdb::NmrOneD292040Specdb::NmrOneD292041Specdb::NmrOneD292042Specdb::NmrOneD292043Specdb::NmrOneD292044Specdb::NmrOneD292045Specdb::NmrOneD292046Specdb::NmrOneD292047Specdb::NmrOneD292048Specdb::NmrOneD292049Specdb::NmrOneD292050Specdb::NmrOneD292051Specdb::NmrOneD292052Specdb::NmrOneD292053Specdb::NmrOneD292054Specdb::MsMs22994Specdb::MsMs22995Specdb::MsMs22996Specdb::MsMs29792Specdb::MsMs29793Specdb::MsMs29794Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, 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-D114.22080510Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75.22102590Yurtsever 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.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.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(18:1(11Z)/19:0) + Water >2 PG(18:1(11Z)/19:0) + PhosphatePW_R0055832 PG(18:1(11Z)/19:0) > Glycerol + CL(18:1(11Z)/19:0/18:1(11Z)/19:0)PW_R005584