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A Radical Approach to Making Unnatural Amino Acids: Conversion of C−S Bonds in Cysteine Derivatives into C−C Bonds
Author(s) -
Wang Yingwei,
Deng LiFan,
Zhang Xia,
Mou ZeDong,
Niu Dawen
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202012503
Subject(s) - radical , chemistry , intramolecular force , cysteine , amino acid , alkyl , bond cleavage , combinatorial chemistry , cleavage (geology) , stereochemistry , photochemistry , organic chemistry , catalysis , biochemistry , materials science , fracture (geology) , enzyme , composite material
Abstract Here we report a general approach to make unnatural amino acids from readily available cysteine derivatives. This method capitalizes on an intramolecular radical substitution process that generates alkyl radicals through C−S cleavage. The resulting alkyl radicals partook in diverse C−C bond forming events. These reactions proceed under mild, photocatalytic conditions at room temperature, and can be performed open to air. The utility of these transformations is further demonstrated in the straightforward synthesis of various unnatural amino acids and peptides that are difficult to access previously.