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 and Goss, R J M (2016) Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water. Chemical Science, 8 (3). pp. 2039-2046. ISSN 2041-6520

[img] PDF - Published Version
Available under License Creative Commons Attribution.

Download (576kB)

Abstract

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.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science
Depositing User: Cristina Pubill Ulldemolins
Date Deposited: 09 Nov 2018 09:36
Last Modified: 02 Jul 2019 14:00
URI: http://sro.sussex.ac.uk/id/eprint/80081

View download statistics for this item

📧 Request an update