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基于胶束的 DNA 导向Suzuki-Miyaura 交叉偶联反应的官能团容忍度及其在 DNA 编码化合物库设计中的应用。

Functional Group Tolerance of a Micellar on-DNA Suzuki-Miyaura Cross-Coupling Reaction for DNA-Encoded Library Design.

机构信息

Cancer Research UK Newcastle Drug Discovery Unit, Chemistry, School of Natural and Environmental Sciences, Newcastle University, Bedson Building, Newcastle upon Tyne NE1 7RU, U.K.

Research Group Medicinal Chemistry, Faculty of Chemistry and Chemical Biology, TU Dortmund University, Otto-Hahn-Straße 6, 44227 Dortmund, Germany.

出版信息

J Org Chem. 2021 Dec 17;86(24):17930-17935. doi: 10.1021/acs.joc.1c02259. Epub 2021 Nov 24.

Abstract

DNA-encoded libraries (DELs) offer great promise for the discovery of new ligands for proteins. Many current reactions used for DEL synthesis do not proceed efficiently over a wide range of substrates. Combining a diverse array of multicomponent reactions with micellar-promoted Suzuki-Miyaura cross-coupling provides a strategy for synthesizing highly diverse DELs with exceptionally high fidelity. These results demonstrate that the micellar Suzuki-Miyaura reaction has exceptional functional group tolerance and broad applicability.

摘要

DNA 编码文库 (DEL) 为发现新的蛋白质配体提供了很大的希望。许多当前用于 DEL 合成的反应在广泛的底物范围内不能有效地进行。将多种多组分反应与胶束促进的铃木-宫浦偶联反应相结合,为合成具有极高保真度的高度多样化的 DEL 提供了一种策略。这些结果表明胶束铃木-宫浦反应具有出色的官能团耐受性和广泛的适用性。

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