Synthesis of methyl (Z)-tetracos-5-enoate and both enantiomers of ethyl (E)-6-methyltetracos-4-enoate: possible intermediates in the biosynthesis of mycolic acids in mycobacteria
✍ Scribed by Gurdyal S. Besra; David E. Minnikin; Paul R. Wheeler; Colin Ratledge
- Book ID
- 103042312
- Publisher
- Elsevier Science
- Year
- 1993
- Tongue
- English
- Weight
- 827 KB
- Volume
- 66
- Category
- Article
- ISSN
- 0009-3084
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✦ Synopsis
The high molecular weight 2-alkyl-3-hydroxy mycolic acids are key structural components of the cell envelope of pathogenic mycobacteria, such as Mycobacterium tuberculosis. A prime target for drug action would be the initial stages where the biosynthetic pathways diverge from those of ordinary fatty acids. It has been postulated that the pathway for the t~-mycolates, without oxygen functions in addition to the hydroxy-acid unit, appears to diverge from (Z)-tetracos-5-enoic acid. The biosynthesis of oxygenated mycolic acids is considered to possibly diverge from (E)-6-(R)-methyltetracos-4-enoic and (E)-6-(S)-methyltetracos-4-enoic acids. This communication describes the synthesis of esters of these acids in order to test their potential role in the biosynthesis of mycolic acids.