2.02012-10-24 09:55:05 -06002015-12-09 12:08:27 -0700ECMDB23710M2MDB004100PG(19:0cycv8c/12:0(3-OH))PG(19:0cycv8c/12:0(3-OH)) 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(19:0cycv8c/12:0(3-OH)), in particular, consists of one heptadec-11-12-cyclo-anoyl chain to the C-1 atom, and one 3-hydroxydodecanoyl 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-(heptadec-11-12-cyclo-anoyl)-2-3-hydroxydodecanoyl-sn-glycero-3-phospho-(1'-glycerol)1-(heptadec-11-12-cyclo-anoyl)-2-3-hydroxydodecanoyl-sn-glycero-3-phosphoglycerol1-(heptadec-11-12-cyclo-anoyl)-2-3-hydroxydodecanoyl-sn-glycero-3-phosphoglycerol1-heptadec-11-12-cyclo-anoyl-2-3-hydroxydodecanoyl-sn-glycero-3-phospho-(1'-glycerol)1-heptadec-11-12-cyclo-anoyl-2-3-hydroxydodecanoyl-sn-glycero-3-phosphoglycerolGPG(19:0/12:0)GPG(31:0)PG(19:0/12:0)PG(31:0)Phosphatidylglycerol(19:0/12:0)Phosphatidylglycerol(31:0)C37H71O11P722.938722.473400104[(2S)-2,3-dihydroxypropoxy][(2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-[(3-hydroxydodecanoyl)oxy]propoxy]phosphinic acid(2S)-2,3-dihydroxypropoxy((2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-[(3-hydroxydodecanoyl)oxy]propoxy)phosphinic acid[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCC)OC(=O)CCCCCCCCCC1CC1CCCCCCInChI=1S/C37H71O11P/c1-3-5-7-9-11-15-19-23-33(39)26-37(42)45-29-35(30-47-49(43,44)46-28-34(40)27-38)48-36(41)24-20-16-13-10-12-14-18-22-32-25-31(32)21-17-8-6-4-2/h31-35,38-40H,3-30H2,1-2H3,(H,43,44)/t31?,32?,33?,34-,35+/m0/s1DBCURBSBXHHYJY-BISNVOBLSA-NSolidMembranelogp6.28logs-6.33solubility3.37e-04 g/llogp8.48pka_strongest_acidic1.89pka_strongest_basic-2.8iupac[(2S)-2,3-dihydroxypropoxy][(2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-[(3-hydroxydodecanoyl)oxy]propoxy]phosphinic acidaverage_mass722.938mono_mass722.473400104smiles[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCC)OC(=O)CCCCCCCCCC1CC1CCCCCCformulaC37H71O11PinchiInChI=1S/C37H71O11P/c1-3-5-7-9-11-15-19-23-33(39)26-37(42)45-29-35(30-47-49(43,44)46-28-34(40)27-38)48-36(41)24-20-16-13-10-12-14-18-22-32-25-31(32)21-17-8-6-4-2/h31-35,38-40H,3-30H2,1-2H3,(H,43,44)/t31?,32?,33?,34-,35+/m0/s1inchikeyDBCURBSBXHHYJY-BISNVOBLSA-Npolar_surface_area169.05refractivity190.32polarizability85.2rotatable_bond_count37acceptor_count7donor_count4physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(19:0cycv8c/12:0(3-OH)/12:0/12:0))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.
PW001992Metabolicphospholipid biosynthesis (CL(19:0cycv8c/12:0(3-OH)/19:0cycv8c/12:0(3-OH)))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.PW001993MetabolicSpecdb::CMs1088273Specdb::EiMs4410Specdb::NmrOneD268728Specdb::NmrOneD268729Specdb::NmrOneD268730Specdb::NmrOneD268731Specdb::NmrOneD268732Specdb::NmrOneD268733Specdb::NmrOneD268734Specdb::NmrOneD268735Specdb::NmrOneD268736Specdb::NmrOneD268737Specdb::NmrOneD268738Specdb::NmrOneD268739Specdb::NmrOneD268740Specdb::NmrOneD268741Specdb::NmrOneD268742Specdb::NmrOneD268743Specdb::NmrOneD268744Specdb::NmrOneD268745Specdb::NmrOneD268746Specdb::NmrOneD268747Specdb::MsMs1246375Specdb::MsMs1246376Specdb::MsMs1246377Specdb::MsMs1361722Specdb::MsMs1361723Specdb::MsMs1361724Kanehisa, 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-D114.22080510Taylor SS, Heath EC. (1969) "The incorporation of beta-hydroxy fatty acids into a phospholipid of Escherichia coli B." J Biol Chem. 244(24):6605-16.4902888Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.ALysophospholipase L2P07000PLDB_ECOLIpldBhttp://ecmdb.ca/proteins/P07000.xmlPhosphatidylglycerophosphatase BP0A924PGPB_ECOLIpgpBhttp://ecmdb.ca/proteins/P0A924.xmlPhosphatidylglycerophosphatase AP18200PGPA_ECOLIpgpAhttp://ecmdb.ca/proteins/P18200.xmlLipid A export ATP-binding/permease protein msbAP60752MSBA_ECOLImsbAhttp://ecmdb.ca/proteins/P60752.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.xmlLipid A export ATP-binding/permease protein msbAP60752MSBA_ECOLImsbAhttp://ecmdb.ca/proteins/P60752.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(19:0cycv8c/12:0(3-OH)) + Water >2 PG(19:0cycv8c/12:0(3-OH)) + PhosphatePW_R005609PG(19:0cycv8c/12:0(3-OH)) + PE(12:0/12:0) > Ethanolamine + CL(19:0cycv8c/12:0(3-OH)/12:0/12:0)PW_R0056102 PG(19:0cycv8c/12:0(3-OH)) > Glycerol + CL(19:0cycv8c/12:0(3-OH)/19:0cycv8c/12:0(3-OH))PW_R005611