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Site‐Directed Asymmetric Quaternization of a Peptide Backbone at a C‐Terminal Azlactone
Author(s) -
Uraguchi Daisuke,
Asai Yoshihiro,
Ooi Takashi
Publication year - 2009
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.200803661
Subject(s) - alkylation , peptide , chemistry , combinatorial chemistry , stereochemistry , stereoselectivity , peptide synthesis , salt (chemistry) , catalysis , organic chemistry , biochemistry
Dual‐purpose activation : Peptide C‐terminal azlactones I undergo stereoselective alkylation with high efficiency by the use of a newly devised chiral tetraaminophosphonium salt as a phase‐transfer catalyst, and the alkylated azlactone products II can be employed directly for peptide ligation (see scheme, LG=leaving group). In this way, a wide range of chiral quaternary α‐amino acid residues can be incorporated at specific sites of a peptide strand.