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Development of a Micellar-Promoted Heck Reaction for the Synthesis of DNA-Encoded Libraries

Lookup NU author(s): Dr Harriet Annabella Stanway-Gordon, Jake Odger, 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

The capability of DNA encoded libraries (DELs) as a method of small molecule hit identification is becoming widely established in drug discovery. While their selection method offers advantages over more traditional means, DELs are limited by the chemistry that can be utilized to construct them. Significant advances in DNA compatible chemistry have been made over the past five years; however such procedures are still often burdened by substrate specificity and/or incomplete conversions, reducing the fidelity of the resulting libraries. One such reaction is the Heck coupling, for which current DNA-compatible protocols are somewhat unreliable. Utilizing micellar technology, we have developed a highly efficient DNA-compatible Heck reaction that proceeds on average to 95% conversion to product across a broad variety of structurally significant building blocks and multiple DNA conjugates. This work continues the application of micellar catalysis to the development of widely applicable, effective DNA-compatible reactions for use in DELs.

Publication metadata

Author(s): Stanway-Gordon HA, Odger JA, Waring MJ

Publication type: Article

Publication status: Published

Journal: Bioconjugate Chemistry

Year: 2023

Volume: 34

Issue: 4

Pages: 756-763

Print publication date: 19/04/2023

Online publication date: 08/03/2023

Acceptance date: 08/03/2023

Date deposited: 21/03/2023

ISSN (print): 1043-1802

ISSN (electronic): 1520-4812

Publisher: American Chemical Society

URL: https://doi.org/10.1021/acs.bioconjchem.3c00051

DOI: 10.1021/acs.bioconjchem.3c00051

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