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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

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posted on 2023-06-09, 15:45 authored by M J Corr, S V Sharma, Cristina Pubill Ulldemolins, R T Bown, P Poirot, D R M Smith, C Cartmell, A Abou Fayad, R J M Goss
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.

History

Publication status

  • Published

File Version

  • Published version

Journal

Chemical Science

ISSN

2041-6520

Publisher

Royal Society of Chemistry

Issue

3

Volume

8

Page range

2039-2046

Department affiliated with

  • Chemistry Publications

Full text available

  • Yes

Peer reviewed?

  • Yes

Legacy Posted Date

2018-11-09

First Open Access (FOA) Date

2018-11-09

First Compliant Deposit (FCD) Date

2018-11-09

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