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Lookup NU author(s): Dr Geoffrey Coxon,
Professor Del Besra,
Professor David Minnikin
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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.
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
ISSN (print): 0009-3084
ISSN (electronic): 1873-2941
Publisher: Elsevier Ireland
PubMed id: 14706739
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