This project consists of three parts. In the first part the synthesis of two mycolic acid diastereomers (I and II) was achieved, thereby completing the full range of the cis-dicyclopropane a-mycolic acid diastereomers.
The second part comprised the development of a new method for the synthesis of the a-alkyl-β-hydroxy fragment of mycolic acids; two novel routes that involved fewer steps were targeted using L-malic as starting material. The first route which was via diethyl malate was achieved in fewer steps without a significant reduction in percentage yield. The second route via dimethyl malate was also completed successfully. Finally, a model cord factor III of a β-hydroxy carboxylic acid without an a-alkyl chain was prepared.
ELISA assays were carried out using the products as antigens to detect antibodies in serum of patients diagnosed with active tuberculois and higher antibody binding signal was observed for II in comparison to I. Good antibody recognition was also observed for III.