The Chirality Chain in Valine: How the Configuration at the Cα Position through the OcisC′CαN Torsional System Leads to Distortion of the Planar Group CαC′(Ocis)Otrans to a Flat Tetrahedron

Abstract

Abstract Solid‐state structures, based on a Cambridge Structural Database (CSD) search, show that there is a CαN/C′Ocis attraction in the torsional system OcisC′CαN of valine, causing a chirality chain. The Cα configuration controls the chirality of the rotation around the C′−Cα bond, which in turn induces a distortion of the planar unit CαC′(O)O to a flat asymmetric tetrahedron. Conformational “reactions” take place in an energy profile with respect to clockwise and counterclockwise rotation around the C′−Cα bond as well as stretching and flattening of the tetrahedron. The molecular property CαN/C′Ocis attraction of valine is maintained in its di‐ and tripeptides.

Keywords

• amino acids
• chirality
• conformation
• peptides
• valine