2.02012-05-31 14:58:08 -06002015-12-09 12:07:47 -0700ECMDB21086M2MDB001502PG(17:0/14:0)PG(17:0/14:0) 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(17:0/14:0), in particular, consists of one heptadecanoyl chain to the C-1 atom, and one tetradecanoyl 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-myristoyl-sn-glycero-3-phosphoglycerol1-heptadecanoyl-2-tetradecanoyl-glycero-3-phospho-(1'-sn-glycerol)1-margaroyl-2-tetradecanoyl-sn-glycero-3-phospho-(1'-glycerol)1-margaroyl-2-tetradecanoyl-sn-glycero-3-phosphoglycerolGPG(17:0/14:0)GPG(31:0)PG(31:0)Phosphatidylglycerol(17:0/14:0)Phosphatidylglycerol(31:0)C37H73O10P708.9433708.494135068[(2S)-2,3-dihydroxypropoxy][(2R)-2-(heptadecanoyloxy)-3-(tetradecanoyloxy)propoxy]phosphinic acid(2S)-2,3-dihydroxypropoxy(2R)-2-(heptadecanoyloxy)-3-(tetradecanoyloxy)propoxyphosphinic acid[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCInChI=1S/C37H73O10P/c1-3-5-7-9-11-13-15-16-17-19-21-23-25-27-29-37(41)47-35(33-46-48(42,43)45-31-34(39)30-38)32-44-36(40)28-26-24-22-20-18-14-12-10-8-6-4-2/h34-35,38-39H,3-33H2,1-2H3,(H,42,43)/t34-,35+/m0/s1XEWGNFBGFJTIKP-OIDHKYIRSA-NInner membraneMembraneOuter membranelogp7.59logs-6.66solubility1.56e-04 g/llogp10.49pka_strongest_acidic1.89pka_strongest_basic-3iupac[(2S)-2,3-dihydroxypropoxy][(2R)-2-(heptadecanoyloxy)-3-(tetradecanoyloxy)propoxy]phosphinic acidaverage_mass708.9433mono_mass708.494135068smiles[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCformulaC37H73O10PinchiInChI=1S/C37H73O10P/c1-3-5-7-9-11-13-15-16-17-19-21-23-25-27-29-37(41)47-35(33-46-48(42,43)45-31-34(39)30-38)32-44-36(40)28-26-24-22-20-18-14-12-10-8-6-4-2/h34-35,38-39H,3-33H2,1-2H3,(H,42,43)/t34-,35+/m0/s1inchikeyXEWGNFBGFJTIKP-OIDHKYIRSA-Npolar_surface_area148.82refractivity190.71polarizability86.13rotatable_bond_count39acceptor_count6donor_count3physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(17:0/16:1(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.
PW001963Metabolicphospholipid biosynthesis IPHOSLIPSYN-PWYSpecdb::CMs1086292Specdb::NmrOneD270038Specdb::NmrOneD270039Specdb::NmrOneD270040Specdb::NmrOneD270041Specdb::NmrOneD270042Specdb::NmrOneD270043Specdb::NmrOneD270044Specdb::NmrOneD270045Specdb::NmrOneD270046Specdb::NmrOneD270047Specdb::NmrOneD270048Specdb::NmrOneD270049Specdb::NmrOneD270050Specdb::NmrOneD270051Specdb::NmrOneD270052Specdb::NmrOneD270053Specdb::NmrOneD270054Specdb::NmrOneD270055Specdb::NmrOneD270056Specdb::NmrOneD270057Specdb::MsMs23579Specdb::MsMs23580Specdb::MsMs23581Specdb::MsMs30377Specdb::MsMs30378Specdb::MsMs30379Keseler, 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(17:0/14:0) + Water >2 PG(17:0/14:0) + PhosphatePW_R005769