Employing Photoredox Catalysis for DNA‐Encoded Chemistry: Decarboxylative Alkylation of α‐Amino Acids,ChemMedChem

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Employing Photoredox Catalysis for DNA‐Encoded Chemistry: Decarboxylative Alkylation of α‐Amino Acids
ChemMedChem ( IF 3.6 ) Pub Date : 2018-08-23 , DOI: 10.1002/cmdc.201800492
Dominik K. Kölmel ₁ , Richard P. Loach ₁ , Thomas Knauber ₁ , Mark E. Flanagan ₁

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A new procedure for the photoredox‐mediated conjugate addition of radicals that can be conveniently generated from α‐amino acids to DNA‐tagged Michael acceptors and styrenes is presented. This C(sp³)−C(sp³) coupling tolerates a broad array of structurally diverse radical precursors, including all of the 20 proteinogenic amino acids. Importantly, this reaction proceeds under mild conditions and in DNA‐compatible aqueous media. Furthermore, the presented reaction conditions are compatible with DNA, making this reaction platform well suited for the construction of DNA‐encoded libraries. The scope and limitations of the chemistry are discussed herein along with proposals for how this methodology might be used to construct DNA‐encoded libraries.

中文翻译：

利用光氧化还原催化进行DNA编码化学：α-氨基酸的脱羧烷基化

提出了一种新的光自由基介导的自由基加成新方法，该自由基可以很容易地从α-氨基酸生成到DNA标记的Michael受体和苯乙烯上。这种C（sp ³）-C（sp ³）偶联可耐受多种结构多样的自由基前体，包括所有20种蛋白原氨基酸。重要的是，该反应在温和条件下和在与DNA相容的水性介质中进行。此外，提出的反应条件与DNA兼容，从而使该反应平台非常适合于DNA编码文库的构建。本文讨论了化学的范围和局限性，以及有关如何使用此方法构建DNA编码文库的建议。

更新日期：2018-08-23

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