2.02015-09-08 19:30:29 -06002015-12-09 12:07:58 -0700ECMDB24390M2MDB006507PG(17:0cycw7c/17:0cycw7c)PG(17:0cycw7c/17:0cycw7c) 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(17:0cycw7c/17:0cycw7c), in particular, consists of two heptadec-9-10-cyclo-anoyl chains at positions C-1 and C-2. 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.C40H75O10P747.004746.509785613[(2R)-2,3-bis({[8-(2-hexylcyclopropyl)octanoyl]oxy})propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid(2R)-2,3-bis({[8-(2-hexylcyclopropyl)octanoyl]oxy})propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCCC1CC1CCCCCCInChI=1S/C40H75O10P/c1-3-5-7-15-21-33-27-35(33)23-17-11-9-13-19-25-39(43)47-31-38(32-49-51(45,46)48-30-37(42)29-41)50-40(44)26-20-14-10-12-18-24-36-28-34(36)22-16-8-6-4-2/h33-38,41-42H,3-32H2,1-2H3,(H,45,46)/t33?,34?,35?,36?,37-,38+/m0/s1OBXHKDVMOWISFV-GWHWHECRSA-Nlogp7.51logs-6.79solubility1.21e-04 g/llogp10.27pka_strongest_acidic1.89pka_strongest_basic-3iupac[(2R)-2,3-bis({[8-(2-hexylcyclopropyl)octanoyl]oxy})propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acidaverage_mass747.004mono_mass746.509785613smiles[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCCC1CC1CCCCCCformulaC40H75O10PinchiInChI=1S/C40H75O10P/c1-3-5-7-15-21-33-27-35(33)23-17-11-9-13-19-25-39(43)47-31-38(32-49-51(45,46)48-30-37(42)29-41)50-40(44)26-20-14-10-12-18-24-36-28-34(36)22-16-8-6-4-2/h33-38,41-42H,3-32H2,1-2H3,(H,45,46)/t33?,34?,35?,36?,37-,38+/m0/s1inchikeyOBXHKDVMOWISFV-GWHWHECRSA-Npolar_surface_area148.82refractivity200.7polarizability88.63rotatable_bond_count38acceptor_count6donor_count3physiological_charge-1formal_charge0phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/17:0cycw7c/17:0cycw7c)"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."PW001078MetabolicSpecdb::CMs1086888Specdb::EiMs3124Specdb::NmrOneD324132Specdb::NmrOneD324133Specdb::NmrOneD324134Specdb::NmrOneD324135Specdb::NmrOneD324136Specdb::NmrOneD324137Specdb::NmrOneD324138Specdb::NmrOneD324139Specdb::NmrOneD324140Specdb::NmrOneD324141Specdb::NmrOneD324142Specdb::NmrOneD324143Specdb::NmrOneD324144Specdb::NmrOneD324145Specdb::NmrOneD324146Specdb::NmrOneD324147Specdb::NmrOneD324148Specdb::NmrOneD324149Specdb::NmrOneD324150Specdb::NmrOneD324151Specdb::MsMs1221751Specdb::MsMs1221752Specdb::MsMs1221753Specdb::MsMs1337410Specdb::MsMs1337411Specdb::MsMs1337412Keseler, 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.xml2 PGP(17:0cycw7c/17:0cycw7c) + Water >2 PG(17:0cycw7c/17:0cycw7c) + PhosphatePW_R005789