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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Veröffentlicht in:	Chemical science (Cambridge) 2017-03, Vol.8 (3), p.2039-2046
Hauptverfasser:	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
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Sprache:	eng
Schlagworte:	Biosynthesis Blending Bromination Cross coupling Metabolites Natural products Precursors Synthesis (chemistry)
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creator	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
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.
doi_str_mv	10.1039/c6sc04423a
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source	DAOJ: Directory of Open Access Journals; PubMed Central (Open access); EZB Electronic Journals Library; PubMed Central Open Access
subjects	Biosynthesis Blending Bromination Cross coupling Metabolites Natural products Precursors Synthesis (chemistry)
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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