Enhanced Metabolic Stability and Protein‐Binding Properties of Artificial α Helices Derived from a Hydrogen‐Bond Surrogate: Application to Bcl‐xL

Abstract

Artificial α helices prepared by the replacement of a hydrogen bond between residues i and i+4 with a carbon–carbon bond can stabilize biologically relevant peptides in helical conformations (1, internal constraint shaded in gray). α Helices based on hydrogen-bond surrogates that mimic Bak BH3 (2, yellow) can bind their expected protein receptor, Bcl-xL (2, green), with high affinity and resist proteolytic degradation. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z501603_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.