Trans-2-Aminocyclohexanols as pH-triggered molecular switches

Abstract

Cyclohexane-based conformationally controlled ionophores, the emerging new class of molecular switches, provide a new and promising approach to allosteric systems with negative cooperativity. Protonation of trans-2-aminocyclohexanols leads to dramatic conformational changes: due to an intramolecular hydrogen bond, a conformer with equatorial position of ammonio- and hydroxy-groups becomes predominant. Thus, these structures can serve as powerful conformational pH-triggers. The trans-2-aminocyclohexanol moiety has been used for pH-triggered conformational switching of a crown ether and a podand, and their complexes with potassium ion. ©ARKAT.