Total synthesis of the post-translationally modified polyazole peptide antibiotic plantazolicin A

Wada, Hiroki and Williams, Huw E. L. and Moody, Christopher J. (2015) Total synthesis of the post-translationally modified polyazole peptide antibiotic plantazolicin A. Angewandte Chemie International Edition, 54 (50). pp. 15147-15151. ISSN 1433-7851

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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).

Item Type: Article
RIS ID: https://nottingham-repository.worktribe.com/output/763668
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.
Keywords: Antibiotics; carbenes; diazo compounds; heterocycles; total synthesis
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: https://doi.org/10.1002/anie.201507062
Depositing User: Bramwell, Roseanna
Date Deposited: 14 Jul 2016 14:47
Last Modified: 04 May 2020 17:19
URI: http://eprints.nottingham.ac.uk/id/eprint/34953

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