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Chemoselective Peptide Cyclization by Traceless Staudinger Ligation
Author(s) -
Kleineweischede Rolf,
Hackenberger Christian P. R.
Publication year - 2008
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.200801514
Subject(s) - trifluoroacetic acid , chemistry , amide , peptide , intramolecular force , borane , combinatorial chemistry , peptide bond , stereochemistry , organic chemistry , biochemistry , catalysis
Two birds with one stone! An intramolecular traceless Staudinger ligation was employed to synthesize cyclic peptides. The final amide bond formation was induced by deprotection of the azidopeptide phosphinothioesters. Treatment with trifluoroacetic acid (TFA) results in the simultaneous removal of the borane along with the protecting groups on the peptide side chains, and chemoselective amide bond cyclization ensues.