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Highly Stereoselective N‐Terminal Functionalization of Small Peptides by Chiral Phase‐Transfer Catalysis
Author(s) -
Ooi Takashi,
Tayama Eiji,
Maruoka Keiji
Publication year - 2003
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.200390167
Subject(s) - alkylation , chemistry , catalysis , chirality (physics) , stereoselectivity , surface modification , phase (matter) , combinatorial chemistry , stereochemistry , schiff base , terminal (telecommunication) , polymer chemistry , organic chemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark , telecommunications , computer science
Virtually complete chirality transfer has been realized in the N‐terminal alkylation of small, Schiff‐base activated peptides under mild phase‐transfer conditions, in which finely tuned chiral quaternary ammonium salts are used as catalysts. Repeated extension and alkylation of the N‐terminal position can lead selectively to nonnatural oligopeptides (see picture).