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Metal‐Free, Regioselective Triazole Ligations that Deliver Locked cis Peptide Mimetics
Author(s) -
Schmieder Peter,
Kühne Ronald,
Rademann Jörg
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.200806390
Subject(s) - regioselectivity , cycloaddition , peptide , chemistry , triazole , click chemistry , combinatorial chemistry , metal , stereochemistry , 1,3 dipolar cycloaddition , organic chemistry , catalysis , biochemistry
Metal‐free triazole turns : 1,5‐Disubstituted peptidyl triazoles are obtained regioselectively from the 1,3‐dipolar cycloaddition of peptidyl phosphoranes and azides. Peptide turns are thus formed that contain a conformationally locked cis peptide bond. Being regioselective and free of heavy metals, this reaction may find broad application in chemical biology and medicinal chemistry.