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
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.