| Description: | CL(12:0(3-OH)/19:iso/12:0(3-OH)/19:iso) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(12:0(3-OH)/19:iso/12:0(3-OH)/19:iso) contains two chains of 3-hydroxydodecanoic acid at the C1 and C3 positions, two chains of 17-methylocatdecanoic acid at the C2 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 Pseudomonas aeruginosa, 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 Pseudomonas aeruginosa, 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. Pseudomonas aeruginosa 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 Pseudomonas aeruginosa and other rod-shaped bacteria. It is known that the polar positioning of the proline transporter ProP and the mechanosensitive ion channel MscS in Pseudomonas aeruginosa is dependent on CL. It is believed that cell shape may influence the localization of CL and the localization of certain membrane proteins. |
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| InChI: | InChI=1S/C71H138O19P2/c1-7-9-11-13-29-37-43-49-63(72)53-70(77)83-57-66(89-68(75)51-45-39-33-27-23-19-15-17-21-25-31-35-41-47-61(3)4)59-87-91(79,80)85-55-65(74)56-86-92(81,82)88-60-67(58-84-71(78)54-64(73)50-44-38-30-14-12-10-8-2)90-69(76)52-46-40-34-28-24-20-16-18-22-26-32-36-42-48-62(5)6/h61-67,72-74H,7-60H2,1-6H3,(H,79,80)(H,81,82)/t63?,64?,65?,66-,67-/m1/s1 |
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| References: |
- De Siervo, A. J. (1969). "Alterations in the phospholipid composition of Escherichia coli B during growth at different temperatures." J Bacteriol 100:1342-1349. Pubmed: 4902814
- 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. Pubmed: 22956318
- Kanehisa, 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. Pubmed: 22080510
- Keseler, 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. Pubmed: 21097882
- Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. Pubmed: 22102590
- Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
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