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Photoinduced Decarboxylative Radical Addition Reactions for Late Stage Functionalization of Peptide Substrates
Author(s) -
FernandezRodriguez Patricia,
Legros Fabien,
Maier Thomas,
Weber Angelika,
Méndez María,
Derdau Volker,
Hessler Gerhard,
Kurz Michael,
VillarGarea Ana,
Ruf Sven
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001178
Subject(s) - chemistry , surface modification , conjugate , derivatization , combinatorial chemistry , peptide , radical , photoredox catalysis , addition reaction , carboxylate , michael reaction , organic chemistry , catalysis , biochemistry , mathematical analysis , mathematics , high performance liquid chromatography , photocatalysis
Photoredox chemistry has greatly stimulated the application of radical based transformations in medicinal chemistry and early drug discovery in recent years. Carboxylate groups have been identified as traceless leaving groups that can be converted into radical intermediates capable of undergoing 1,4‐conjugate addition reactions to Michael acceptors. Herein, we show the successful C‐terminal derivatization of small peptide substrates by using this methodology in a parallel synthesis setting. Finally, we outline a general strategy for the γ‐homologation of several drugs derived from α‐amino acids in a late stage functionalization (LSF) approach.