Total synthesis of the post-translationally modified polyazole peptide antibiotic plantazolicin A
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...
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| Format: | Article |
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Wiley-VCH Verlag
2015
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| Online Access: | https://eprints.nottingham.ac.uk/34953/ |
| _version_ | 1848794969646563328 |
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| author | Wada, Hiroki Williams, Huw E. L. Moody, Christopher J. |
| author_facet | Wada, Hiroki Williams, Huw E. L. Moody, Christopher J. |
| author_sort | Wada, Hiroki |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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). |
| first_indexed | 2025-11-14T19:24:38Z |
| format | Article |
| id | nottingham-34953 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T19:24:38Z |
| publishDate | 2015 |
| publisher | Wiley-VCH Verlag |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-349532020-05-04T17:19:23Z https://eprints.nottingham.ac.uk/34953/ Total synthesis of the post-translationally modified polyazole peptide antibiotic plantazolicin A Wada, Hiroki Williams, Huw E. L. Moody, Christopher J. 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). Wiley-VCH Verlag 2015-10-16 Article PeerReviewed Wada, Hiroki, 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 Antibiotics; carbenes; diazo compounds; heterocycles; total synthesis http://onlinelibrary.wiley.com/doi/10.1002/anie.201507062/abstract doi:10.1002/anie.201507062 doi:10.1002/anie.201507062 |
| spellingShingle | Antibiotics; carbenes; diazo compounds; heterocycles; total synthesis Wada, Hiroki Williams, Huw E. L. Moody, Christopher J. Total synthesis of the post-translationally modified polyazole peptide antibiotic plantazolicin A |
| title | Total synthesis of the post-translationally modified polyazole peptide antibiotic plantazolicin A |
| title_full | Total synthesis of the post-translationally modified polyazole peptide antibiotic plantazolicin A |
| title_fullStr | Total synthesis of the post-translationally modified polyazole peptide antibiotic plantazolicin A |
| title_full_unstemmed | Total synthesis of the post-translationally modified polyazole peptide antibiotic plantazolicin A |
| title_short | Total synthesis of the post-translationally modified polyazole peptide antibiotic plantazolicin A |
| title_sort | total synthesis of the post-translationally modified polyazole peptide antibiotic plantazolicin a |
| topic | Antibiotics; carbenes; diazo compounds; heterocycles; total synthesis |
| url | https://eprints.nottingham.ac.uk/34953/ https://eprints.nottingham.ac.uk/34953/ https://eprints.nottingham.ac.uk/34953/ |