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.
- Location
-
Deutsche Nationalbibliothek Frankfurt am Main
- Extent
-
Online-Ressource
- Language
-
Englisch
- Bibliographic citation
-
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)
- Creator
-
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
-
10.1002/chem.202403767
- URN
-
urn:nbn:de:101:1-2411151323156.423940348704
- Rights
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
-
15.08.2025, 7:34 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Lysenko, Vladyslav
- Son, Sangkeun
- Theriault, Monique E.
- Slingerland, Cornelis J.
- Hauk, Glenn
- Cleenewerk, Laurence
- Speer, Alexander
- Berger, James M.
- Lewis, Kim
- Martin, Nathaniel I.
Other Objects (12)
Total Synthesis of the Marine Natural Product rac-Dibromophakellstatin
Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis
Heterocycles in natural product synthesis
Organic and natural product synthesis
Modern Natural Product Synthesis : Overcoming Difficulties
Total synthesis of grayanane natural products
Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery
Total synthesis and cytotoxicity of the marine natural product malevamide D and a photoreactive analog
Transition-metal and organocatalysis in natural product synthesis
Studies in natural product synthesis : toward the total synthesis of maoecrystal V and caribenol A and total synthesis of sandresolide B and the proposed structure of Trichodermatide A
Total Synthesis and Structural Revision of the Piperarborenines
Total Synthesis and Structural Assignment of (−)‐Fusaequisin A
Total Synthesis of the Marine Natural Product rac-Dibromophakellstatin
Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis
Heterocycles in natural product synthesis
Organic and natural product synthesis
Modern Natural Product Synthesis : Overcoming Difficulties
Total synthesis of grayanane natural products
Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery
Total synthesis and cytotoxicity of the marine natural product malevamide D and a photoreactive analog
Transition-metal and organocatalysis in natural product synthesis
Studies in natural product synthesis : toward the total synthesis of maoecrystal V and caribenol A and total synthesis of sandresolide B and the proposed structure of Trichodermatide A
Total Synthesis and Structural Revision of the Piperarborenines
Total Synthesis and Structural Assignment of (−)‐Fusaequisin A
Total Synthesis of the Marine Natural Product rac-Dibromophakellstatin
Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis
Heterocycles in natural product synthesis
Organic and natural product synthesis
Modern Natural Product Synthesis : Overcoming Difficulties
Total synthesis of grayanane natural products
Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery
Total synthesis and cytotoxicity of the marine natural product malevamide D and a photoreactive analog
Transition-metal and organocatalysis in natural product synthesis
Studies in natural product synthesis : toward the total synthesis of maoecrystal V and caribenol A and total synthesis of sandresolide B and the proposed structure of Trichodermatide A
Total Synthesis and Structural Revision of the Piperarborenines