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Synthesis and properties of methyl 5-(1′R,2′S)-(2- octadecylcycloprop-1-yl)pentanoate and other ω-19 chiral cyclopropane fatty acids and esters related to mycobacterial mycolic acids

Lookup NU author(s): Dr Geoffrey Coxon, Professor Del Besra, Professor David Minnikin

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Abstract

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 14C-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. © 2003 Elsevier Ireland Ltd. All rights reserved.

Publication metadata

Author(s): Coxon GD, Al Dulayymi JR, Morehouse C, Brennan PJ, Besra GS, Baird MS, Minnikin DE

Publication type: Article

Publication status: Published

Journal: Chemistry and Physics of Lipids

Year: 2004

Volume: 127

Issue: 1

Pages: 35-46

ISSN (print): 0009-3084

ISSN (electronic): 1873-2941

Publisher: Elsevier Ireland

URL: http://dx.doi.org/10.1016/j.chemphyslip.2003.09.001

DOI: 10.1016/j.chemphyslip.2003.09.001

PubMed id: 14706739

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