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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...

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Autores principales: 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.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
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.
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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
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
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
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
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
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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