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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Authors
Corr, M JSharma, S V
Pubill-Ulldemolins, C
Bown, R T
Poirot, P
Smith, D R M
Cartmell, C
Abou Fayad, A
Goss, R J M
Issue Date
2017-03-01
Metadata
Show full item recordAbstract
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.Citation
Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water. 2017, 8 (3):2039-2046 Chem SciAffiliation
Hel,holtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr.7, 38124 Braunschweig, Germany.Journal
Chemical sciencePubMed ID
28451322Type
ArticleLanguage
enISSN
2041-6520ae974a485f413a2113503eed53cd6c53
10.1039/c6sc04423a
Scopus Count
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- Creative Commons