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Late‐Stage Peptide Macrocyclization by Palladium‐Catalyzed Site‐Selective C−H Olefination of Tryptophan
Author(s) -
Bai Zengbing,
Cai Chuangxu,
Sheng Wangjian,
Ren Yuxiang,
Wang Huan
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202007226
Subject(s) - alkene , chemistry , palladium , peptide , tryptophan , catalysis , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , amino acid
Transition‐metal‐catalyzed C−H activation has shown potential in the functionalization of peptides with expanded structural diversity. Herein, the development of late‐stage peptide macrocyclization methods by palladium‐catalyzed site‐selective C(sp 2 )−H olefination of tryptophan residues at the C2 and C4 positions is reported. This strategy utilizes the peptide backbone as endogenous directing groups and provides access to peptide macrocycles with unique Trp–alkene crosslinks.