1. Employing Photoredox Catalysis for DNA-Encoded Chemistry: Decarboxylative Alkylation of α-Amino Acids.
- Author
-
Kölmel DK, Loach RP, Knauber T, and Flanagan ME
- Subjects
- Acrylamides chemistry, Alkylation, Amines chemical synthesis, Amino Acids radiation effects, Catalysis, Coordination Complexes chemistry, Coordination Complexes radiation effects, Decarboxylation, Free Radicals chemistry, Iridium chemistry, Light, Oxidation-Reduction, Proof of Concept Study, Amino Acids chemistry, DNA chemistry
- Abstract
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(sp
3 )-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., (© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)- Published
- 2018
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