2.02012-05-31 14:55:49 -06002015-12-09 12:07:04 -0700ECMDB21041M2MDB001457PG(14:0/19:0)PG(14:0/19:0) 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(14:0/19:0), in particular, consists of one tetradecanoyl 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-myristoyl-2--sn-glycero-3-phosphoglycerol1-myristoyl-2-nonadecanoyl-sn-glycero-3-phosphoglycerol1-tetradecanoyl-2-nonadecanoyl-glycero-3-phospho-(1'-sn-glycerol)1-tetradecanoyl-2-nonadecanoyl-sn-glycero-3-phospho-(1'-glycerol)1-tetradecanoyl-2-nonadecanoyl-sn-glycero-3-phosphoglycerolGPG(14:0/19:0)GPG(33:0)PG(33:0)Phosphatidylglycerol(14:0/19:0)Phosphatidylglycerol(33:0)C39H77O10P736.9964736.525435196[(2S)-2,3-dihydroxypropoxy][(2R)-3-(nonadecanoyloxy)-2-(tetradecanoyloxy)propoxy]phosphinic acid(2S)-2,3-dihydroxypropoxy(2R)-3-(nonadecanoyloxy)-2-(tetradecanoyloxy)propoxyphosphinic acid[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCInChI=1S/C39H77O10P/c1-3-5-7-9-11-13-15-16-17-18-19-21-22-24-26-28-30-38(42)46-34-37(35-48-50(44,45)47-33-36(41)32-40)49-39(43)31-29-27-25-23-20-14-12-10-8-6-4-2/h36-37,40-41H,3-35H2,1-2H3,(H,44,45)/t36-,37+/m0/s1DTAKYBBKAGWHOP-PQQNNWGCSA-NInner membraneMembraneOuter membranelogp8.05logs-6.78solubility1.22e-04 g/llogp11.38pka_strongest_acidic1.89pka_strongest_basic-3iupac[(2S)-2,3-dihydroxypropoxy][(2R)-3-(nonadecanoyloxy)-2-(tetradecanoyloxy)propoxy]phosphinic acidaverage_mass736.9964mono_mass736.525435196smiles[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCformulaC39H77O10PinchiInChI=1S/C39H77O10P/c1-3-5-7-9-11-13-15-16-17-18-19-21-22-24-26-28-30-38(42)46-34-37(35-48-50(44,45)47-33-36(41)32-40)49-39(43)31-29-27-25-23-20-14-12-10-8-6-4-2/h36-37,40-41H,3-35H2,1-2H3,(H,44,45)/t36-,37+/m0/s1inchikeyDTAKYBBKAGWHOP-PQQNNWGCSA-Npolar_surface_area148.82refractivity199.91polarizability89.46rotatable_bond_count41acceptor_count6donor_count3physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(19:0/16:1(9Z)/14:0/14:0))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.
PW001983Metabolicphospholipid biosynthesis IPHOSLIPSYN-PWYSpecdb::CMs1087141Specdb::NmrOneD292795Specdb::NmrOneD292796Specdb::NmrOneD292797Specdb::NmrOneD292798Specdb::NmrOneD292799Specdb::NmrOneD292800Specdb::NmrOneD292801Specdb::NmrOneD292802Specdb::NmrOneD292803Specdb::NmrOneD292804Specdb::NmrOneD292805Specdb::NmrOneD292806Specdb::NmrOneD292807Specdb::NmrOneD292808Specdb::NmrOneD292809Specdb::NmrOneD292810Specdb::NmrOneD292811Specdb::NmrOneD292812Specdb::NmrOneD292813Specdb::NmrOneD292814Specdb::MsMs26264Specdb::MsMs26265Specdb::MsMs26266Specdb::MsMs32822Specdb::MsMs32823Specdb::MsMs32824Keseler, 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(14:0/19:0) + Water >2 PG(14:0/19:0) + PhosphatePW_R005770