Title

trans-2-Aminocyclohexanols as pH-Triggered Molecular Switches

Poster Number

26

Format

Poster Presentation

Abstract/Artist Statement

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 an intramolecular hydrogen bond, a conformer with equatorial position of ammonio- and hydroxy-groups becomes predominant. This ‘impulse’ is mechanically transmitted by the structure of the molecule, inducing a conformational change in the second site, thus altering its properties, e.g. decreasing its affinity to an appropriate guest, or changing a distance between groups of atoms. The variation of NR2 groups allows a broad tuning of the conformational equilibrium. These structures can serve as powerful conformational pH-triggers, and may find many applications, such as a design of switchable ionophores for membrane transport, or of triggerable lipid vesicles for drug and gene delivery.

Location

Pacific Geosciences Center

Start Date

5-5-2007 1:00 PM

End Date

5-5-2007 3:00 PM

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May 5th, 1:00 PM May 5th, 3:00 PM

trans-2-Aminocyclohexanols as pH-Triggered Molecular Switches

Pacific Geosciences Center

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 an intramolecular hydrogen bond, a conformer with equatorial position of ammonio- and hydroxy-groups becomes predominant. This ‘impulse’ is mechanically transmitted by the structure of the molecule, inducing a conformational change in the second site, thus altering its properties, e.g. decreasing its affinity to an appropriate guest, or changing a distance between groups of atoms. The variation of NR2 groups allows a broad tuning of the conformational equilibrium. These structures can serve as powerful conformational pH-triggers, and may find many applications, such as a design of switchable ionophores for membrane transport, or of triggerable lipid vesicles for drug and gene delivery.