2.02012-05-31 14:55:24 -06002015-12-09 17:00:39 -0700ECMDB21033M2MDB001449PG(19:0/17:0)PG(19:0/17:0) 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(19:0/17:0), in particular, consists of one nonadecanoyl chain to the C-1 atom, and one heptadecanoyl 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--2-heptadecanoyl-sn-glycero-3-phosphoglycerol1-nonadecanoyl-2-heptadecanoyl-glycero-3-phospho-(1'-sn-glycerol)1-nonadecanoyl-2-heptadecanoyl-sn-glycero-3-phosphoglycerol1-nonadecanoyl-2-margaroyl-sn-glycero-3-phospho-(1'-glycerol)1-nonadecanoyl-2-margaroyl-sn-glycero-3-phosphoglycerolGPG(19:0/17:0)GPG(36:0)PG(36:0)Phosphatidylglycerol(19:0/17:0)Phosphatidylglycerol(36:0)C42H83O10P779.09778.572385871[(2R)-2,3-dihydroxypropoxy][(2R)-3-(heptadecanoyloxy)-2-(nonadecanoyloxy)propoxy]phosphinic acid(2R)-2,3-dihydroxypropoxy((2R)-3-(heptadecanoyloxy)-2-(nonadecanoyloxy)propoxy)phosphinic acid[H][C@@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCInChI=1S/C42H83O10P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-42(46)52-40(38-51-53(47,48)50-36-39(44)35-43)37-49-41(45)33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h39-40,43-44H,3-38H2,1-2H3,(H,47,48)/t39-,40-/m1/s1VRXBINAFDUHENA-XRSDMRJBSA-NInner membraneMembraneOuter membranelogp8.60logs-7.03solubility7.31e-05 g/llogp12.72pka_strongest_acidic1.89pka_strongest_basic-3iupac[(2R)-2,3-dihydroxypropoxy][(2R)-3-(heptadecanoyloxy)-2-(nonadecanoyloxy)propoxy]phosphinic acidaverage_mass779.09mono_mass778.572385871smiles[H][C@@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCformulaC42H83O10PinchiInChI=1S/C42H83O10P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-42(46)52-40(38-51-53(47,48)50-36-39(44)35-43)37-49-41(45)33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h39-40,43-44H,3-38H2,1-2H3,(H,47,48)/t39-,40-/m1/s1inchikeyVRXBINAFDUHENA-XRSDMRJBSA-Npolar_surface_area148.82refractivity213.71polarizability95.85rotatable_bond_count44acceptor_count6donor_count3physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(19:iso/17:0cycw7c/19:0/19:0))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.
PW002007Metabolicphospholipid biosynthesis IPHOSLIPSYN-PWYSpecdb::CMs1085951Specdb::NmrOneD334778Specdb::NmrOneD334779Specdb::NmrOneD334780Specdb::NmrOneD334781Specdb::NmrOneD334782Specdb::NmrOneD334783Specdb::NmrOneD334784Specdb::NmrOneD334785Specdb::NmrOneD334786Specdb::NmrOneD334787Specdb::NmrOneD334788Specdb::NmrOneD334789Specdb::NmrOneD334790Specdb::NmrOneD334791Specdb::NmrOneD334792Specdb::NmrOneD334793Specdb::NmrOneD334794Specdb::NmrOneD334795Specdb::NmrOneD334796Specdb::NmrOneD334797Specdb::MsMs1297630Specdb::MsMs1297631Specdb::MsMs1297632Specdb::MsMs1412251Specdb::MsMs1412252Specdb::MsMs1412253Keseler, 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(19:0/17:0) + Water >2 PG(19:0/17:0) + PhosphatePW_R005803