trans-2-Aminocyclohexanols as pH-triggered molecular switches

Authors

Barbora Brazdova, University of the PacificFollow
Sombo Koo
Yuen-Shan Wong
Andrey V. Samoshin
Ningrong Zhang, University of the PacificFollow
Andreas H. Franz, University of the PacificFollow
Xin Guo, University of the PacificFollow
Vyacheslav V. Samoshin, University of the PacificFollow

Document Type

Poster

Conference Title/Conference Publication

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

Organization

American Chemical Society (ACS)

Location

San Francisco, CA

Conference Dates

September 10-14, 2006

Date of Presentation

9-11-2006

Abstract

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.

Comments

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Recommended Citation

Brazdova, Barbora; Koo, Sombo; Wong, Yuen-Shan; Samoshin, Andrey V.; Zhang, Ningrong; Franz, Andreas H.; Guo, Xin; and Samoshin, Vyacheslav V., "trans-2-Aminocyclohexanols as pH-triggered molecular switches" (2006). School of Pharmacy Faculty Presentations. 394.
https://scholarlycommons.pacific.edu/phs-facpres/394