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*

*Bijbehorende auteur voor dit werk

OnderzoeksoutputAcademicpeer review

6 Citaten (Scopus)
67 Downloads (Pure)

Samenvatting

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.

Originele taal-2English
Pagina's (van-tot) 7555-7560
Aantal pagina's6
TijdschriftAngewandte Chemie (International ed. in English)
Volume59
Nummer van het tijdschrift19
Vroegere onlinedatum18-feb-2020
DOI's
StatusPublished - 4-mei-2020

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