2.02012-08-23 12:32:37 -06002015-12-09 11:20:13 -0700ECMDB22798M2MDB003188CL(17:0cycw7c/15:0cyclo/14:0/14:0)CL(17:0cycw7c/15:0cyclo/14:0/14:0) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(17:0cycw7c/15:0cyclo/14:0/14:0) contains one chain of (heptadec-9-10-cyclo-anoyl) at the C1 position, one chain of cis-9,10-Methylenetetradecanoic acid at the C2 position, two chains of tetradecanoic acid at the C3 and C4 positions. While the theoretical charge of cardiolipins is -2, under normal physiological conditions (pH near 7), the molecule may carry only one negative charge. In prokaryotes such as E. coli, the enzyme known as diphosphatidylglycerol synthase catalyses the transfer of the phosphatidyl moiety of one phosphatidylglycerol to the free 3'-hydroxyl group of another, with the elimination of one molecule of glycerol. In E. coli, which acylates its glycerophospholipids with acyl chains ranging in length from 12 to 19 carbons and possibly containing an unsaturation, or a cyclopropane group more than 100 possible CL molecular species are theoretically possible. E. coli membranes consist of ~5% cardiolipin (CL), 20-25% phosphatidylglycerol (PG), and 70-80% phosphatidylethanolamine (PE) as well as smaller amounts of phosphatidylserine (PS). CL is distributed between the two leaflets of the bilayers and is located preferentially at the poles and septa in E. coli and other rod-shaped bacteria. It is known that the polar positioning of the proline transporter ProP and the mechanosensitive ion channel MscS in E. coli is dependent on CL. It is believed that cell shape may influence the localization of CL and the localization of certain membrane proteins.1'-[1-heptadec-9-10-cyclo-anoyl-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phospho],3'-[1,2-dimyristoyl-rac-glycero-3-phospho]-glycerol1'-[1-heptadec-9-10-cyclo-anoyl-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phospho],3'-[1,2-ditetradecanoyl-rac-glycero-3-phospho]-glycerolCardiolipin(17:0/15:0/14:0/14:0)Cardiolipin(60:0)CL(1'-[17:0cycw7c/15:0cyclo],3'-[14:0/14:0])CL(17:0/15:0/14:0/14:0)CL(60:0)C69H130O17P21293.731292.878326722[(2R)-2,3-bis(tetradecanoyloxy)propoxy][(2R)-3-({[(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid(2R)-2,3-bis(tetradecanoyloxy)propoxy((2R)-3-{[(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid[H][C@@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCCC1CC1CCCCInChI=1S/C69H130O17P2/c1-5-9-13-16-18-20-22-24-26-32-39-47-66(71)79-55-64(85-68(73)49-41-33-27-25-23-21-19-17-14-10-6-2)57-83-87(75,76)81-53-63(70)54-82-88(77,78)84-58-65(86-69(74)50-42-35-29-31-37-45-60-51-59(60)43-12-8-4)56-80-67(72)48-40-34-28-30-38-46-62-52-61(62)44-36-15-11-7-3/h59-65,70H,5-58H2,1-4H3,(H,75,76)(H,77,78)/t59?,60?,61?,62?,63-,64-,65-/m1/s1DMOUOROLSTZHEI-ZXBFYKBLSA-NSolidMembranelogp8.42logs-7.35solubility5.78e-05 g/llogp20.38pka_strongest_acidic1.59pka_strongest_basic-3.4iupac[(2R)-2,3-bis(tetradecanoyloxy)propoxy][(2R)-3-({[(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acidaverage_mass1293.73mono_mass1292.878326722smiles[H][C@@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCCC1CC1CCCCformulaC69H130O17P2inchiInChI=1S/C69H130O17P2/c1-5-9-13-16-18-20-22-24-26-32-39-47-66(71)79-55-64(85-68(73)49-41-33-27-25-23-21-19-17-14-10-6-2)57-83-87(75,76)81-53-63(70)54-82-88(77,78)84-58-65(86-69(74)50-42-35-29-31-37-45-60-51-59(60)43-12-8-4)56-80-67(72)48-40-34-28-30-38-46-62-52-61(62)44-36-15-11-7-3/h59-65,70H,5-58H2,1-4H3,(H,75,76)(H,77,78)/t59?,60?,61?,62?,63-,64-,65-/m1/s1inchikeyDMOUOROLSTZHEI-ZXBFYKBLSA-Npolar_surface_area236.95refractivity347.88polarizability154.07rotatable_bond_count70acceptor_count9donor_count3physiological_charge-2formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis CL(17:0cycw7c/15:0cyclo/14:0/14:0)"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."PW001650Metabolicphospholipid biosynthesis IPHOSLIPSYN-PWYSpecdb::EiMs3190Specdb::MsMs1286278Specdb::MsMs1286279Specdb::MsMs1286280Specdb::MsMs1401076Specdb::MsMs1401077Specdb::MsMs1401078Keseler, 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-D114.22080510De Siervo, A. J. (1969). "Alterations in the phospholipid composition of Escherichia coli B during growth at different temperatures." J Bacteriol 100:1342-1349.4902814Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.ACardiolipin synthaseP0A6H8CLS_ECOLIclshttp://ecmdb.ca/proteins/P0A6H8.xmlPutative cardiolipin synthase ybhOP0AA84YBHO_ECOLIybhOhttp://ecmdb.ca/proteins/P0AA84.xmlCardiolipin synthase CP75919CLSC_ECOLIclsChttp://ecmdb.ca/proteins/P75919.xmlPG(14:0/14:0) + PE(15:0/17:0cycw7c) > CL(17:0cycw7c/15:0cyclo/14:0/14:0) + EthanolaminePW_R004575Luria-Bertani (LB) mediaShake flask0.05822uM0.037 oCK12Stationary phase cultures (overnight culture)Garrett, T. A., O'Neill, A. C., Hopson, M. L. (2012). "Quantification of cardiolipin molecular species in Escherichia coli lipid extracts using liquid chromatography/electrospray ionization mass spectrometry." Rapid Commun Mass Spectrom 26:2267-2274.22956318