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Goss_et_al-2019-Chemistry_-_A_European_Journal.pdf (1.69 MB)

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

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posted on 2023-06-09, 18:00 authored by Cristina Pubill Ulldemolins, Sunil V Sharma, Christopher Cartmell, Jinlian Zhao, Paco Cárdenas, Rebecca J M Goss
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.

History

Publication status

  • Published

File Version

  • Accepted version

Journal

Chemistry - A European Journal

ISSN

0947-6539

Publisher

Wiley

Department affiliated with

  • Chemistry Publications

Full text available

  • Yes

Peer reviewed?

  • Yes

Legacy Posted Date

2019-06-07

First Open Access (FOA) Date

2020-05-24

First Compliant Deposit (FCD) Date

2019-06-06

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