Total Synthesis and Structural Reassignment of the Antitubercular Natural Product Evybactin
Abstract: The escalating threat posed by antibiotic resistance is a global concern and underscores the need for new antibiotics. In this context, the recent discovery of evybactin, a nonribosomal depsipeptide antibiotic that selectively and potently inhibits the growth of M. tuberculosis, is particularly noteworthy. Here, we present the first total synthesis of this natural product, along with a revision of its assigned structure. Our studies revealed a disparity between the structure originally proposed for evybactin and its actual configuration. Specifically, the 3‐methylhistidine residue present in the evybactin core macrocycle was found to be of the d‐configuration rather than the previously assigned l‐His (Me). Having addressed this, we further optimized our solid‐phase synthetic route to provide access to evybactin on a multi‐hundred‐milligram scale. Access to such quantities will allow for more comprehensive studies with this promising antibiotic.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Total Synthesis and Structural Reassignment of the Antitubercular Natural Product Evybactin ; day:14 ; month:11 ; year:2024 ; extent:6
Chemistry - a European journal ; (14.11.2024) (gesamt 6)
- Urheber
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Lysenko, Vladyslav
Son, Sangkeun
Theriault, Monique E.
Slingerland, Cornelis J.
Hauk, Glenn
Cleenewerk, Laurence
Speer, Alexander
Berger, James M.
Lewis, Kim
Martin, Nathaniel I.
- DOI
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10.1002/chem.202403767
- URN
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urn:nbn:de:101:1-2411151323156.423940348704
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:34 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Lysenko, Vladyslav
- Son, Sangkeun
- Theriault, Monique E.
- Slingerland, Cornelis J.
- Hauk, Glenn
- Cleenewerk, Laurence
- Speer, Alexander
- Berger, James M.
- Lewis, Kim
- Martin, Nathaniel I.
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