Total Synthesis of a Mycolic Acid from Mycobacterium tuberculosis

Nabil Tahiri, Peter Fodran, Dhineshkumar Jayaraman, Jeffrey Buter, Martin D Witte, Tonatiuh A Ocampo, D Branch Moody, Ildiko Van Rhijn, Adriaan J Minnaard*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

2 Citations (Scopus)
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Abstract

In Mycobacterium tuberculosis, mycolic acids and their glycerol, glucose, and trehalose esters ("cord factor") form the main part of the mycomembrane. Despite their first isolation almost a century ago, full stereochemical evaluation is lacking, as is a scalable synthesis required for accurate immunological, including vaccination, studies. Herein, we report an efficient, convergent, gram-scale synthesis of four stereo-isomers of a mycolic acid and its glucose ester. Binding to the antigen presenting protein CD1b and T cell activation studies are used to confirm the antigenicity of the synthetic material. The absolute stereochemistry of the syn-methoxy methyl moiety in natural material is evaluated by comparing its optical rotation with that of synthetic material.

Original languageEnglish
Pages (from-to) 7555-7560
Number of pages6
JournalAngewandte Chemie (International ed. in English)
Volume59
Issue number19
Early online date18-Feb-2020
DOIs
Publication statusPublished - 4-May-2020

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