Evidence for CCl/CBr⋅⋅⋅π Interactions as an Important Contribution to Protein–Ligand Binding Affinity

✍ Scribed by Hans Matter; Marc Nazaré; Stefan Güssregen; David W. Will; Herman Schreuder; Armin Bauer; Matthias Urmann; Kurt Ritter; Michael Wagner; Volkmar Wehner

• Book ID: 102729129
• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 719 KB
• Volume: 48
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.200806219

✦ Synopsis

Abstract

Attractive chlorine: Noncovalent interactions between chlorine or bromine atoms and aromatic rings in proteins open up a new method for the manipulation of molecular recognition. Substitution at distinct positions of two factor Xa inhibitors improves the free energy of binding by interaction with a tyrosine unit. The generality of this motif was underscored by multiple crystal structures as well as high‐level quantum chemical calculations (see picture).magnified image