Coxon, G.D. and Al Dulayymi, J.R. and Morehouse, C. and Brennan, P.J. and Besra, G.S. and Baird, M.S. and Minnikin, D.E. (2004) Synthesis and properties of methyl 5-(1R,2S)-(2-octadecylcycloprop-1-yl)pentanoate and other ω-19 chiral cyclopropane fatty acids and esters related to mycobacterial mycolic acids. Chemistry and Physics of Lipids, 127 (1). pp. 35-46. ISSN 0009-3084Full text not available in this repository. (Request a copy from the Strathclyde author)
A 23–26-carbon chain length range of ω-19 (1′R,2′S) cyclopropane fatty acids, related to mycobacterial mycolic acids, has been prepared. The key cyclopropyl intermediate, (1′R,2′S)-(Z)-1-formyl-2-octadecylcyclopropane, underwent Wittig chemistry with various reagents to provide vinylic precursors, which were selectively reduced to the corresponding saturated ω-19 cyclopropane fatty acids or esters. The 24-carbon ω-19 cyclopropane ester was made by chain elongation of the 23-carbon ester. Saturated and unsaturated chiral cyclopropane acids and esters were assayed, using wall extracts of Mycobacterium smegmatis; the incorporation of -acetate was used to measure inhibition or stimulation of mycolic acid synthesis. Minor inhibition (2–3%) was shown by the 23- and 24-carbon saturated esters; all the other compounds were stimulants. The most effective (38–55%) stimulators of mycolate synthesis were the unsaturated esters with 23- and 26-carbons and the saturated and unsaturated 25-carbon acids.
|Keywords:||fatty acids, biosynthetic inhibitors, mycolic acids, chiral cyclopropane , Pharmacy and materia medica, Biochemistry, Cell Biology, Organic Chemistry, Molecular Biology|
|Subjects:||Medicine > Pharmacy and materia medica|
|Department:||Faculty of Science > Strathclyde Institute of Pharmacy and Biomedical Sciences|
|Depositing user:||Pure Administrator|
|Date Deposited:||27 Feb 2012 14:18|
|Last modified:||29 Apr 2016 09:08|