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Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water
The blending together of synthetic chemistry with natural product biosynthesis represents a potentially powerful approach to synthesis; to enable this, further synthetic tools and methodologies are needed. To this end, we have explored the first Sonogashira cross-coupling to halotryptophans in water...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5398305/ https://www.ncbi.nlm.nih.gov/pubmed/28451322 http://dx.doi.org/10.1039/c6sc04423a |
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author | Corr, M. J. Sharma, S. V. Pubill-Ulldemolins, C. Bown, R. T. Poirot, P. Smith, D. R. M. Cartmell, C. Abou Fayad, A. Goss, R. J. M. |
author_facet | Corr, M. J. Sharma, S. V. Pubill-Ulldemolins, C. Bown, R. T. Poirot, P. Smith, D. R. M. Cartmell, C. Abou Fayad, A. Goss, R. J. M. |
author_sort | Corr, M. J. |
collection | PubMed |
description | The blending together of synthetic chemistry with natural product biosynthesis represents a potentially powerful approach to synthesis; to enable this, further synthetic tools and methodologies are needed. To this end, we have explored the first Sonogashira cross-coupling to halotryptophans in water. Broad reaction scope is demonstrated and we have explored the limits of the scope of the reaction. We have demonstrated this methodology to work excellently in the modification of model tripeptides. Furthermore, through precursor directed biosynthesis, we have generated for the first time a new to nature brominated natural product bromo-cystargamide, and demonstrated the applicability of our reaction conditions to modify this novel metabolite. |
format | Online Article Text |
id | pubmed-5398305 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-53983052017-04-27 Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water Corr, M. J. Sharma, S. V. Pubill-Ulldemolins, C. Bown, R. T. Poirot, P. Smith, D. R. M. Cartmell, C. Abou Fayad, A. Goss, R. J. M. Chem Sci Chemistry The blending together of synthetic chemistry with natural product biosynthesis represents a potentially powerful approach to synthesis; to enable this, further synthetic tools and methodologies are needed. To this end, we have explored the first Sonogashira cross-coupling to halotryptophans in water. Broad reaction scope is demonstrated and we have explored the limits of the scope of the reaction. We have demonstrated this methodology to work excellently in the modification of model tripeptides. Furthermore, through precursor directed biosynthesis, we have generated for the first time a new to nature brominated natural product bromo-cystargamide, and demonstrated the applicability of our reaction conditions to modify this novel metabolite. Royal Society of Chemistry 2017-03-01 2016-11-11 /pmc/articles/PMC5398305/ /pubmed/28451322 http://dx.doi.org/10.1039/c6sc04423a Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Chemistry Corr, M. J. Sharma, S. V. Pubill-Ulldemolins, C. Bown, R. T. Poirot, P. Smith, D. R. M. Cartmell, C. Abou Fayad, A. Goss, R. J. M. Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water |
title | Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water
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title_full | Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water
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title_fullStr | Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water
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title_full_unstemmed | Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water
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title_short | Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water
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title_sort | sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5398305/ https://www.ncbi.nlm.nih.gov/pubmed/28451322 http://dx.doi.org/10.1039/c6sc04423a |
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