2.02012-05-31 14:57:15 -06002015-12-09 17:01:08 -0700ECMDB21069M2MDB001485PG(17:0/18:1(11Z))PG(17:0/18:1(11Z)) 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(17:0/18:1(11Z)), in particular, consists of one heptadecanoyl chain to the C-1 atom, and one 11Z-octadecenoyl 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-heptadecanoyl-2-vaccenoyl-sn-glycero-3-phosphoglycerol1-margaroyl-2-(11Z-octadecenoyl)-sn-glycero-3-phospho-(1'-glycerol)1-margaroyl-2-(11Z-octadecenoyl)-sn-glycero-3-phosphoglycerolGPG(17:0/18:1)GPG(35:1)PG(17:0/18:1)PG(35:1)Phosphatidylglycerol(17:0/18:1)Phosphatidylglycerol(35:1)C41H79O10P763.047762.541085742[(2R)-2,3-dihydroxypropoxy][(2R)-2-(heptadecanoyloxy)-3-[(11Z)-octadec-11-enoyloxy]propoxy]phosphinic acid(2R)-2,3-dihydroxypropoxy((2R)-2-(heptadecanoyloxy)-3-[(11Z)-octadec-11-enoyloxy]propoxy)phosphinic acid[H][C@@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCCCInChI=1S/C41H79O10P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-40(44)48-36-39(37-50-52(46,47)49-35-38(43)34-42)51-41(45)33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h13,15,38-39,42-43H,3-12,14,16-37H2,1-2H3,(H,46,47)/b15-13-/t38-,39-/m1/s1OIQAMORTNGQUSS-WRKYLRESSA-NInner membraneMembraneOuter membranelogp8.37logs-6.94solubility8.76e-05 g/llogp11.91pka_strongest_acidic1.89pka_strongest_basic-3iupac[(2R)-2,3-dihydroxypropoxy][(2R)-2-(heptadecanoyloxy)-3-[(11Z)-octadec-11-enoyloxy]propoxy]phosphinic acidaverage_mass763.047mono_mass762.541085742smiles[H][C@@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCCCformulaC41H79O10PinchiInChI=1S/C41H79O10P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-40(44)48-36-39(37-50-52(46,47)49-35-38(43)34-42)51-41(45)33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h13,15,38-39,42-43H,3-12,14,16-37H2,1-2H3,(H,46,47)/b15-13-/t38-,39-/m1/s1inchikeyOIQAMORTNGQUSS-WRKYLRESSA-Npolar_surface_area148.82refractivity210.23polarizability91.98rotatable_bond_count42acceptor_count6donor_count3physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(17:0cycw7c/18:1(9Z)/17:0cycw7c/17:0cycw7c))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.PW001465Metabolicphospholipid biosynthesis (CL(18:1(9Z)/16:0/17:0cycw7c/16:0))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.PW001584Metabolicphospholipid biosynthesis IPHOSLIPSYN-PWYSpecdb::CMs1089229Specdb::NmrOneD340328Specdb::NmrOneD340329Specdb::NmrOneD340330Specdb::NmrOneD340331Specdb::NmrOneD340332Specdb::NmrOneD340333Specdb::NmrOneD340334Specdb::NmrOneD340335Specdb::NmrOneD340336Specdb::NmrOneD340337Specdb::NmrOneD340338Specdb::NmrOneD340339Specdb::NmrOneD340340Specdb::NmrOneD340341Specdb::NmrOneD340342Specdb::NmrOneD340343Specdb::NmrOneD340344Specdb::NmrOneD340345Specdb::NmrOneD340346Specdb::NmrOneD340347Specdb::MsMs1229599Specdb::MsMs1229600Specdb::MsMs1229601Specdb::MsMs1345156Specdb::MsMs1345157Specdb::MsMs1345158Keseler, 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.xmlCardiolipin synthase CP75919CLSC_ECOLIclsChttp://ecmdb.ca/proteins/P75919.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.xmlPE(17:0cycw7c/17:0cycw7c) + PG(17:0/18:1(11Z)) > Ethanolamine + CL(17:0cycw7c/18:1(9Z)/17:0cycw7c/17:0cycw7c)PW_R005019PG(17:0/18:1(11Z)) + PE(16:0/16:0) > CL(18:1(9Z)/16:0/17:0cycw7c/16:0) + EthanolaminePW_R0051002 PGP(17:0/18:1(11Z)) + Water >2 PG(17:0/18:1(11Z)) + PhosphatePW_R005748