Skip to main content
trans-2-Aminocyclohexanols as pH-triggered molecular switches
232nd National Meeting of the American Chemical Society (ACS)
  • Barbora Brazdova, University of the Pacific
  • Sombo Koo
  • Yuen-Shan Wong
  • Andrey V. Samoshin
  • Ningrong Zhang, University of the Pacific
  • Andreas H. Franz, University of the Pacific
  • Xin Guo, University of the Pacific
  • Vyacheslav V. Samoshin, University of the Pacific
Document Type
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.
Citation Information
Barbora Brazdova, Sombo Koo, Yuen-Shan Wong, Andrey V. Samoshin, et al.. "trans-2-Aminocyclohexanols as pH-triggered molecular switches" 232nd National Meeting of the American Chemical Society (ACS) (2006) ISSN: 2572-6803
Available at: