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β-Turn Mimics by Chemical Ligation
Author(s) -
Selma Crecente-Garcia,
Albane Neckebroeck,
J. Stephen Clark,
Brian O. Smith,
Andrew R. Thomson
Publication year - 2020
Publication title -
organic letters
Language(s) - Uncategorized
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c01427
Subject(s) - chemistry , ligation , chemical ligation , combinatorial chemistry , reductive amination , amination , turn (biochemistry) , peptide , nanotechnology , organic chemistry , biochemistry , catalysis , microbiology and biotechnology , materials science , biology
We report a simple reductive amination protocol to ligate two peptides, while simultaneously installing a β-turn mimic at the ligation junction. This strategy uses commercially available materials, mild chemical conditions, and a chemoselective ligation reaction of unprotected peptide substrates accessed through standard solid phase methods. This system was implemented in a designed β-hairpin system, and biophysical analysis demonstrates effective mimicry of the β-turn.

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