"Triazole Bridge": Disulfide-Bond Replacement by Ruthenium-Catalyzed Formation of 1,5-Disubstituted 1,2,3-Triazoles

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 yielde...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Angewandte Chemie International Edition 2011-05, Vol.50 (22), p.5207-5211
Hauptverfasser:	Empting, Martin, Avrutina, Olga, Meusinger, Reinhard, Fabritz, Sebastian, Reinwarth, Michael, Biesalski, Markus, Voigt, Stephan, Buntkowsky, Gerd, Kolmar, Harald
Format:	Artikel
Sprache:	eng
Schlagworte:	Amino Acid Sequence Catalysis Click Chemistry disulfide bridges Disulfides - chemistry Peptides - chemical synthesis Peptides - chemistry Peptidomimetics Ruthenium Ruthenium - chemistry SFTI-1 Triazoles - chemistry Trypsin - chemistry Trypsin - metabolism trypsin inhibition Trypsin Inhibitors - chemistry
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	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.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201008142