ArticleAngewandte Chemie (International ed. in English)2020
Total Synthesis of a Mycolic Acid from Mycobacterium tuberculosis.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 28 citations in OpenAlex.
- A conserved human CD4+ T cell subset recognizing the mycobacterial adjuvant trehalose monomycolate.The Journal of clinical investigation · 2024Article
- Establishment of CD1b-restricted immunity to lipid antigens in the pulmonary response toInfection and immunity · 2024Article
- Asymmetric Total Synthesis and Structural Revision of DATAngewandte Chemie (International ed. in English) · 2024Article
- Effect of Mycolic Acids on Host Immunity and Lipid Metabolism.International journal of molecular sciences · 2023Review
- Article
- Chemical Synthesis of Cell Wall Constituents ofChemical reviews · 2021Review
- Sensing of mycobacterial arabinogalactan by galectin-9 exacerbates mycobacterial infection.EMBO reports · 2021Article
- T Cells Specific for a Mycobacterial Glycolipid Expand after Intravenous Bacillus Calmette-Guérin Vaccination.Journal of immunology (Baltimore, Md. : 1950) · 2021Article
- Total Synthesis of a Mycolic Acid from Mycobacterium tuberculosis.Angewandte Chemie (International ed. in English) · 2020Article
Corrections and comments
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Authors and funding
9 authors at 2 institutions in 2 countries.
Funding
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.
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Registered trials
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