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Copper(I)‐Mediated Denitrogenative Macrocyclization for the Synthesis of Cyclic α 3 β‐Tetrapeptide Analogues
Author(s) -
Chen ChunChi,
Wang ShengFu,
Su YungYu,
Lin Yuya A.,
Lin PoChiao
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201700339
Subject(s) - tetrapeptide , chemistry , ketenimine , intramolecular force , amidine , stereochemistry , cyclic peptide , amine gas treating , combinatorial chemistry , histone deacetylase , peptide , histone , biochemistry , organic chemistry , gene
A copper(I)‐mediated denitrogenative reaction has been successfully developed for the preparation of cyclic tetrapeptides. The key reactive intermediate, ketenimine, triggers intramolecular cyclization through attack of the terminal amine group to generate an internal β‐amino acid with an amidine linkage. The chemistry developed herein provides a new synthetic route for the preparation of cyclic α 3 β‐tetrapeptide analogues that contain important biological properties and results in rich structural information being obtained for conformational studies. With the success of this copper(I)‐catalyzed macrocyclization, two histone deacetylase inhibitor analogues consisting of the cyclic α 3 β‐tetrapeptide framework have been successfully synthesized.