Total Synthesis of a Mycolic Acid from Mycobacterium tuberculosis

Nabil Tahiri, Peter Fodran, Dhineshkumar Jayaraman, Jeffrey Buter, Martin Witte, Tonatiuh Ocampo, Branch Moody, Ildiko van Rhijn, Adriaan Minnaard

Research output: Contribution to journalArticleAcademicpeer-review


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
JournalAngewandte Chemie International Edition
Issue number19
Publication statusPublished - 18 Feb 2020
Externally publishedYes


  • organic chemistry
  • total synthesis
  • natural product
  • tuberculosis
  • immunology


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