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Solid‐Phase S N Ar Macrocyclizations To Give Turn–Extended‐Turn Peptidomimetics
Author(s) -
Feng Yangbo,
Burgess Kevin
Publication year - 1999
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(19991105)5:11<3261::aid-chem3261>3.0.co;2-h
Subject(s) - turn (biochemistry) , nucleophilic aromatic substitution , peptidomimetic , electrophile , chemistry , nucleophile , combinatorial chemistry , amino acid , stereochemistry , molecule , nucleophilic substitution , organic chemistry , catalysis , biochemistry , peptide
An optimized set of conditions was developed for the synthesis of β ‐turn mimics 1 by S N Ar macrocyclizations. These allow efficient production of molecules containing two amino acids (to mimic part of a turn region) fused with a turn‐inducing fragment. The turn‐inducing fragment is formed from amino acids with nucleophilic side chains and the S N Ar electrophile. This methodology facilitates production of focussed libraries based on target protein structures.