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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container_issue 3
container_start_page 2039
container_title Chemical science (Cambridge)
container_volume 8
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 DOAJ Directory of Open Access Journals; PubMed Central Open Access; EZB-FREE-00999 freely available EZB journals; PubMed Central
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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