2.02015-09-08 19:30:20 -06002015-12-09 12:07:47 -0700ECMDB24386M2MDB006503PG(16:1(9Z)/19:0cycv8c)PG(16:1(9Z)/19:0cycv8c) 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(16:1(9Z)/19:0cycv8c), in particular, consists of one 9Z-hexadecenoyl chain to the C-1 atom, and one heptadec-11-12-cyclo-anoyl 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.C41H77O10P761.031760.525435677[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy]phosphinic acid(2S)-2,3-dihydroxypropoxy((2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy)phosphinic acid[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCInChI=1S/C41H77O10P/c1-3-5-7-9-10-11-12-13-14-15-18-22-26-30-41(45)51-39(35-50-52(46,47)49-33-38(43)32-42)34-48-40(44)29-25-21-19-16-17-20-24-28-37-31-36(37)27-23-8-6-4-2/h11-12,36-39,42-43H,3-10,13-35H2,1-2H3,(H,46,47)/b12-11-/t36?,37?,38-,39+/m0/s1MNSRXAPUXKJQIK-OWIVCOGVSA-Nlogp7.99logs-6.85solubility1.08e-04 g/llogp11.13pka_strongest_acidic1.89pka_strongest_basic-3iupac[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-{[10-(2-hexylcyclopropyl)decanoyl]oxy}propoxy]phosphinic acidaverage_mass761.031mono_mass760.525435677smiles[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCformulaC41H77O10PinchiInChI=1S/C41H77O10P/c1-3-5-7-9-10-11-12-13-14-15-18-22-26-30-41(45)51-39(35-50-52(46,47)49-33-38(43)32-42)34-48-40(44)29-25-21-19-16-17-20-24-28-37-31-36(37)27-23-8-6-4-2/h11-12,36-39,42-43H,3-10,13-35H2,1-2H3,(H,46,47)/b12-11-/t36?,37?,38-,39+/m0/s1inchikeyMNSRXAPUXKJQIK-OWIVCOGVSA-Npolar_surface_area148.82refractivity208.32polarizability90.62rotatable_bond_count40acceptor_count6donor_count3physiological_charge-1formal_charge0phospholipid biosynthesis (CL(16:1(9Z)/19:0cycv8c/16:1(9Z)/19:0cycv8c))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.
PW002017MetabolicSpecdb::CMs1085829Specdb::NmrOneD316121Specdb::NmrOneD316122Specdb::NmrOneD316123Specdb::NmrOneD316124Specdb::NmrOneD316125Specdb::NmrOneD316126Specdb::NmrOneD316127Specdb::NmrOneD316128Specdb::NmrOneD316129Specdb::NmrOneD316130Specdb::NmrOneD316131Specdb::NmrOneD316132Specdb::NmrOneD316133Specdb::NmrOneD316134Specdb::NmrOneD316135Specdb::NmrOneD316136Specdb::NmrOneD316137Specdb::NmrOneD316138Specdb::NmrOneD316139Specdb::NmrOneD316140Specdb::MsMs1314499Specdb::MsMs1314500Specdb::MsMs1314501Specdb::MsMs1428985Specdb::MsMs1428986Specdb::MsMs1428987Keseler, 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.xmlCardiolipin synthaseP0A6H8CLS_ECOLIclshttp://ecmdb.ca/proteins/P0A6H8.xmlPutative cardiolipin synthase ybhOP0AA84YBHO_ECOLIybhOhttp://ecmdb.ca/proteins/P0AA84.xml2 PGP(16:1(9Z)/19:0cycv8c) + Water >2 PG(16:1(9Z)/19:0cycv8c) + PhosphatePW_R0057842 PG(16:1(9Z)/19:0cycv8c) > CL(16:1(9Z)/19:0cycv8c/16:1(9Z)/19:0cycv8c) + GlycerolPW_R005785