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Total Synthesis of the Posttranslationally Modified Polyazole Peptide Antibiotic Plantazolicin A

Wada, Hiroki; Williams, Huw E. L.; Moody, Christopher J.

Authors

Hiroki Wada

Huw E. L. Williams

Christopher J. Moody



Abstract

The power of rhodium carbene methodology in chemistry is demonstrated by the synthesis of a structurally complex polyazole antibiotic. Plantazolicin A, a novel soil bacterium metabolite, comprises a linear array of 10 five-membered rings in two pentacyclic regions that derive from ribosomal peptide synthesis followed by extensive post-translational modification. The compound possesses potent antimicrobial activity, and is selectively active against the anthrax causing organism. A conceptually different synthesis of plantazolicin A is reported in which the key steps are the use of rhodium(II)-catalyzed reactions of diazocarbonyl compounds to generate up to six of the seven oxazole rings of the antibiotic. NMR Spectroscopic studies and molecular modeling, reveal a likely dynamic hairpin conformation with a hinge region around the two isoleucine residues.The compound has modest activity against methicillin-resistant Staphylococcus aureus (MRSA).

Journal Article Type Article
Publication Date Oct 16, 2015
Journal Angewandte Chemie International Edition
Print ISSN 1433-7851
Electronic ISSN 1433-7851
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 54
Issue 50
Pages 15147-15151
APA6 Citation Wada, H., Williams, H. E. L., & Moody, C. J. (2015). Total Synthesis of the Posttranslationally Modified Polyazole Peptide Antibiotic Plantazolicin A. Angewandte Chemie International Edition, 54(50), 15147-15151. https://doi.org/10.1002/anie.201507062
DOI https://doi.org/10.1002/anie.201507062
Keywords Antibiotics; carbenes; diazo compounds; heterocycles; total synthesis
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/anie.201507062/abstract
Copyright Statement Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by-nc/4.0
Additional Information This is the peer reviewed version of the following article: Wada, H., Williams, H. E. L. and Moody, C. J. (2015), Total Synthesis of the Posttranslationally Modified Polyazole Peptide Antibiotic Plantazolicin A. Angew. Chem. Int. Ed., 54: 15147–15151. doi:10.1002/anie.201507062, which has been published in final form at [http://onlinelibrary.wi...nie.201507062/abstract. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by-nc/4.0





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