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Heck Diversification of Indole-Based Substrates under Aqueous Conditions: From Indoles to Unprotected Halo-tryptophans and Halo-tryptophans in Natural Product Derivatives
Univ St Andrews, Dept Chem, St Andrews KY16 9ST, Fife, Scotland;Univ St Andrews, BSRC, St Andrews KY16 9ST, Fife, Scotland;Univ Sussex, Sch Life Sci, Dept Chem, Brighton BN1 9QJ, E Sussex, England.
Univ St Andrews, Dept Chem, St Andrews KY16 9ST, Fife, Scotland;Univ St Andrews, BSRC, St Andrews KY16 9ST, Fife, Scotland.
Univ St Andrews, Dept Chem, St Andrews KY16 9ST, Fife, Scotland;Univ St Andrews, BSRC, St Andrews KY16 9ST, Fife, Scotland.
Univ St Andrews, Dept Chem, St Andrews KY16 9ST, Fife, Scotland;Univ St Andrews, BSRC, St Andrews KY16 9ST, Fife, Scotland.
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2019 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 25, no 46, p. 10866-10875Article in journal (Refereed) Published
Abstract [en]

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 brominated antibiotic (bromo-pacidamycin), as well as a marine sponge metabolite, barettin.

Place, publisher, year, edition, pages
2019. Vol. 25, no 46, p. 10866-10875
Keywords [en]
aqueous cross-coupling, barettin, Heck reaction, natural product modification, halo-tryptophan
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-394275DOI: 10.1002/chem.201901327ISI: 000481420300015PubMedID: 31125453OAI: oai:DiVA.org:uu-394275DiVA, id: diva2:1358245
Funder
EU, Horizon 2020, No. 679849EU, European Research Council, FP7/2007-2013/ERC grant agreement no 614779 GenoChemeticsEU, FP7, Seventh Framework Programme, CXAQAvailable from: 2019-10-07 Created: 2019-10-07 Last updated: 2019-10-07Bibliographically approved

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