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“Triazole Bridge”: Disulfide‐Bond Replacement by Ruthenium‐Catalyzed Formation of 1,5‐Disubstituted 1,2,3‐Triazoles
Author(s) -
Empting Martin,
Avrutina Olga,
Meusinger Reinhard,
Fabritz Sebastian,
Reinwarth Michael,
Biesalski Markus,
Voigt Stephan,
Buntkowsky Gerd,
Kolmar Harald
Publication year - 2011
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.201008142
Subject(s) - ruthenium , peptidomimetic , disulfide bond , chemistry , catalysis , combinatorial chemistry , 1,2,4 triazole , triazole , click chemistry , peptide , polymer chemistry , organic chemistry , biochemistry
A good impression : A modular approach using a ruthenium(II) catalyst during peptide synthesis gives rigid and well‐defined triazole bridges as tailor‐made substitutes for natural disulfide bridges (see structures). The corresponding modification of the monocyclic sunflower trypsin inhibitor‐1 yielded an equally potent peptidomimetic containing a redox stable 1,5‐disubstituted 1,2,3‐triazole bridge.