trans-2-Aminocyclohexanols as pH-triggered molecular switches

Document Type


Conference Title/Conference Publication

232nd National Meeting of the American Chemical Society (ACS)


American Chemical Society (ACS)


San Francisco, CA

Conference Dates

September 10-14, 2006

Date of Presentation



The cyclohexane-based conformationally controlled 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 a strong intramolecular hydrogen bond, a conformer with equatorial ammonio- and hydroxy-groups becomes predominant. This ‘impulse' is mechanically transmitted by the structure of the molecule to induce a conformational change of a remote site, thus altering its properties. Thus, these structures can serve as powerful conformational pH-triggers. The variation of NR2 groups allows a broad tuning of the conformational equilibrium, which was studied by NMR. Heterotropic allosteric systems with high negative cooperativity may find many applications, e.g in the triggerable lipid vesicles for drug and gene delivery.

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