Switchable Oligopeptide Helix

  • ChemPubSoc Europe Logo
  • Author: Chemistry – An Asian Journal
  • Published Date: 21 September 2018
  • Source / Publisher: Chemistry – An Asian Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Switchable Oligopeptide Helix

Dynamic helical oligomers and polymers are mostly build of achiral repeating units, but with a chiral residue covalently or noncovalently bound to one chain end. This generates either a right-handed (P)-helix or a left-handed (M)-helix in a domino-like fashion. One of the most interesting features of dynamic helical oligomers and polymers is a long-range chiral information transfer.

Akio Urushima, Naoki Ousaka, and Eiji Yashima, Nagoya University, Japan, have found a solvent-induced switching of the helix handedness of a lactam-bridged dynamic helical oligopeptide. It has different chiral units at both ends, e.g., an axially chiral unit at the N-terminus and an L-amino acid at the C-terminus (pictured). The handedness of the helix partially switches when the solvent is changed from CH2Cl2 to dimethyl sulfoxide (DMSO) or vice versa.


This effect is a result of competitive helix-inducing biases—like a tug-of-war between two chiral twisting forces generated from the two chiral terminal units. The chiral domino effect from the N-terminal unit can be switched on and off, as shown in the picture. The effect is triggered by the solvent‐induced breaking of a specific intramolecular hydrogen bond. These findings may provide a rational design strategy for chirality-switchable asymmetric catalysts, and could also contribute to understanding the mechanism of solvent-induced helix-inversion in other helical systems.


 

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