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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

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).

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

Journal Article Type Article
Acceptance Date Sep 14, 2015
Online Publication Date Oct 16, 2015
Publication Date Oct 16, 2015
Deposit Date Jul 14, 2016
Publicly Available Date Jul 14, 2016
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
DOI https://doi.org/10.1002/anie.201507062
Keywords Antibiotics; carbenes; diazo compounds; heterocycles; total synthesis
Public URL http://eprints.nottingham.ac.uk/id/eprint/34953
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.wiley.com/doi/10.1002/anie.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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