J. Am. Chem. Soc., 129 (3), 466 -467, 2007. 10.1021/ja067148o S0002-7863(06)07148-4
Web Release Date: December 29, 2006

Copyright © 2006 American Chemical Society

Azidoproline Containing Helices: Stabilization of the Polyproline II Structure by a Functionalizable Group

Michael Kümin, Louis-Sebastian Sonntag, and Helma Wennemers*

Department of Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland

helma.wennemers@unibas.ch

Received October 5, 2006

Abstract:

The conformation and functionalizability of 4-azidoproline containing polyprolines was studied. The conformational analyses demonstrate that the PPII helix is stabilized by (4R)Azp and destabilized by (4S)Azp. Functionalization of Azp containing polyprolines was accomplished efficiently in a differential fashion by "click chemistry", rendering Azp containing polyprolines attractive molecular scaffolds.


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