2.02012-05-31 14:57:31 -06002015-12-09 12:07:28 -0700ECMDB21074M2MDB001490PG(16:0/17:0)PG(16:0/17:0) 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(16:0/17:0), in particular, consists of one hexadecanoyl 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-hexadecanoyl-2-heptadecanoyl-glycero-3-phospho-(1'-sn-glycerol)1-hexadecanoyl-2-margaroyl-sn-glycero-3-phospho-(1'-glycerol)1-hexadecanoyl-2-margaroyl-sn-glycero-3-phosphoglycerol1-palmitoyl-2-heptadecanoyl-sn-glycero-3-phosphoglycerolGPG(16:0/17:0)GPG(33:0)PG(33:0)Phosphatidylglycerol(16:0/17:0)Phosphatidylglycerol(33:0)C39H77O10P736.9964736.525435196[(2S)-2,3-dihydroxypropoxy][(2R)-3-(heptadecanoyloxy)-2-(hexadecanoyloxy)propoxy]phosphinic acid(2S)-2,3-dihydroxypropoxy(2R)-3-(heptadecanoyloxy)-2-(hexadecanoyloxy)propoxyphosphinic acid[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCInChI=1S/C39H77O10P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-38(42)46-34-37(35-48-50(44,45)47-33-36(41)32-40)49-39(43)31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h36-37,40-41H,3-35H2,1-2H3,(H,44,45)/t36-,37+/m0/s1ILTOCVUJZXMWRV-PQQNNWGCSA-NInner membraneMembraneOuter membranelogp8.04logs-6.78solubility1.22e-04 g/llogp11.38pka_strongest_acidic1.89pka_strongest_basic-3iupac[(2S)-2,3-dihydroxypropoxy][(2R)-3-(heptadecanoyloxy)-2-(hexadecanoyloxy)propoxy]phosphinic acidaverage_mass736.9964mono_mass736.525435196smiles[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCformulaC39H77O10PinchiInChI=1S/C39H77O10P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-38(42)46-34-37(35-48-50(44,45)47-33-36(41)32-40)49-39(43)31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h36-37,40-41H,3-35H2,1-2H3,(H,44,45)/t36-,37+/m0/s1inchikeyILTOCVUJZXMWRV-PQQNNWGCSA-Npolar_surface_area148.82refractivity199.91polarizability89.55rotatable_bond_count41acceptor_count6donor_count3physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(17:0/16:1(9Z)/16:0/16:0))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.
PW001964Metabolicphospholipid biosynthesis IPHOSLIPSYN-PWYSpecdb::CMs1085184Specdb::NmrOneD315201Specdb::NmrOneD315202Specdb::NmrOneD315203Specdb::NmrOneD315204Specdb::NmrOneD315205Specdb::NmrOneD315206Specdb::NmrOneD315207Specdb::NmrOneD315208Specdb::NmrOneD315209Specdb::NmrOneD315210Specdb::NmrOneD315211Specdb::NmrOneD315212Specdb::NmrOneD315213Specdb::NmrOneD315214Specdb::NmrOneD315215Specdb::NmrOneD315216Specdb::NmrOneD315217Specdb::NmrOneD315218Specdb::NmrOneD315219Specdb::NmrOneD315220Specdb::MsMs26978Specdb::MsMs26979Specdb::MsMs26980Specdb::MsMs33536Specdb::MsMs33537Specdb::MsMs33538Keseler, 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.xmlPGP(16:0/16:0) + Water > PG(16:0/17:0) + PhosphatePW_R004075PE(16:0/18:0) + PG(16:0/17:0) > Ethanolamine + CL(18:1(9Z)/16:0/18:1(9Z)/19:0cycv8c)PW_R004519PE(16:0/18:0) + PG(16:0/17:0) > Ethanolamine + CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/17:0cycw7c)PW_R004612PE(16:0/18:0) + PG(16:0/17:0) > Ethanolamine + CL(17:0cycw7c/18:1(9Z)/17:0cycw7c/19:0cycv8c)PW_R0043852 PGP(16:0/17:0) + Water >2 PG(16:0/17:0) + PhosphatePW_R005780