Heck diversification of indole based substrates under aqueous conditions: from indoles to unprotected halo-tryptophans and halo-tryptophans in a natural and a new to nature natural product

Pubill Ulldemolins, Cristina, Sharma, Sunil V, Cartmell, Christopher, Zhao, Jinlian, Cárdenas, Paco and Goss, Rebecca J M (2019) Heck diversification of indole based substrates under aqueous conditions: from indoles to unprotected halo-tryptophans and halo-tryptophans in a natural and a new to nature natural product. Chemistry - A European Journal. ISSN 0947-6539

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Abstract

The blending of synthetic chemistry with biosynthetic
processes provides a powerful approach to synthesis. Biosynthetic halogenation and synthetic cross-coupling have great potential to be used together, for small molecule generation, access to natural product analogues and as a tool for chemical biology. However to enable enhanced generality of this approach, further synthetic tools are needed. Though considerable research has been invested in the diversification of phenylalanine and tyrosine, functionalisation of tryptophans thorough cross-coupling has been largely neglected.
Tryptophan is a key residue in many biologically active natural products and peptides; in proteins it is key to fluorescence, and dominates protein folding. To this end, we have explored the Heck cross-coupling of halo-indoles and halo-tryptophans in water, showing broad reaction scope. We have demonstrated the ability to use this methodology in the functionalisation of a new to nature
brominated antibiotic (bromo-pacidamycin), as well as a marine sponge metabolite, barettin.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: Cristina Pubill Ulldemolins
Date Deposited: 07 Jun 2019 14:23
Last Modified: 24 May 2020 01:00
URI: http://sro.sussex.ac.uk/id/eprint/84154

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