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Micelle-Mediated Sonogashira Coupling for DNA-Encoded Library Synthesis

Lookup NU author(s): Dr Jessica Graham, Dr Harriet Annabella Stanway-Gordon, Professor Mike Waring

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This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).

Abstract

© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.DNA-Encoded Libraries (DELs) are becoming widely established as a hit identification strategy for drug discovery campaigns. Their successful application relies on the availability and efficiency of the reactions that can be carried out on DNA. These reactions should proceed with high conversion to the desired product and have a broad substrate scope to synthesise chemically diverse and drug-like DELs. The Sonogashira coupling provides a unique means of coupling an sp-hybridized carbon centre to an aryl halide and methods to achieve this reaction on DNA are highly desirable. We report the application of our micellar technology for on-DNA chemistry to the Sonogashira reaction. This method gives highly efficient conversions for the coupling of (hetero)aromatic and aliphatic alkynes to (hetero)aryl iodides and bromides allowing the preparation of highly diverse DELs.

Publication metadata

Author(s): Graham JS, Stanway-Gordon HA, Waring MJ

Publication type: Article

Publication status: Published

Journal: Chemistry - A European Journal

Year: 2023

Volume: 29

Issue: 42

Print publication date: 26/07/2023

Online publication date: 15/05/2023

Acceptance date: 15/05/2023

Date deposited: 03/07/2023

ISSN (print): 0947-6539

ISSN (electronic): 1521-3765

Publisher: John Wiley and Sons Inc

URL: https://doi.org/10.1002/chem.202300603

DOI: 10.1002/chem.202300603

Data Access Statement: The data that support the findings of this study are available in the supplementary material of this article.

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