Synthesis of single enantiomers of ketomycolic acids

Abstract

Mycolic acids, long chain fatty acids often containing 70 to 90 carbons, are major constituents of the cell envelope of M tuberculosis and other pathogenic mycobacteria. Their presence is thought to explain the characteristic resistance of these mycobacteria to most antibiotics and other chemotherapeutic agents.
The syntheses of single enantiomers of the following mycolic acid derivatives were achieved; cis-cyclopropane keto-mycolic acid (A), a-methyl-trans-cyclopropane ketomycolic acid (B), cis-cyclopropane keto-meromycolaldehyde (C), a-methyl-trans-cyclopropane keto-meromycolaldehyde (D), a-methyl-trans-alkene keto-mycolic acid (E) and related hydroxy-mycolic acids. However, the synthesis of a' -mycolic acid (F) failed.

The synthesis of single enantiomers of mycolic acids will help to prove the stereochemistry of the natural ones, and tests of their biological activities may offer the development of new methods for the diagnosis and treatment of TB and related diseases.

Date of Award	Sept 2007
Original language	English
Awarding Institution	Bangor University
Sponsors	School of Chemistry, Bangor University & Abant Izzet Baysal University, Turkey
Supervisor	Mark Baird (Supervisor)