Title

Novel Molecular Switches Based on Hydroxypiperidines

Poster Number

23

Format

Poster Presentation

Abstract/Artist Statement

The conformationally controlled molecular switches provide a new and promising approach to substances and materials with controllable properties. In particular, derivatives of cyclohexane and other six-membered cycles with certain configuration of substituents are able to model allosteric systems with negative cooperativity. Thus, a protonation of hydroxypiperidines leads to conformational shift: due to a strong intramolecular hydrogen bond, conformers (B) becomes stabilized. This ‘impulse’ is mechanically transmitted by the structure of the molecule to induce a conformational change of remote groups, thus altering their properties. These structures can serve as powerful conformational pH-triggers. Variation of substituents allows a tuning of the conformational equilibrium and its pH-sensitivity, as studied by 1H NMR. The conformationally controlled molecular switches may find many applications, e.g. in a design of switchable ionophores for membrane transport, or of the triggerable lipid vesicles for drug and gene delivery. The Dean’s Undergraduate Research Award from College of the Pacific, UOP, and the Scholarly/Artistic Activity Grant, and the Eberhardt Research Fellowship from UOP are gratefully acknowledged.

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

Novel Molecular Switches Based on Hydroxypiperidines

Pacific Geosciences Center

The conformationally controlled molecular switches provide a new and promising approach to substances and materials with controllable properties. In particular, derivatives of cyclohexane and other six-membered cycles with certain configuration of substituents are able to model allosteric systems with negative cooperativity. Thus, a protonation of hydroxypiperidines leads to conformational shift: due to a strong intramolecular hydrogen bond, conformers (B) becomes stabilized. This ‘impulse’ is mechanically transmitted by the structure of the molecule to induce a conformational change of remote groups, thus altering their properties. These structures can serve as powerful conformational pH-triggers. Variation of substituents allows a tuning of the conformational equilibrium and its pH-sensitivity, as studied by 1H NMR. The conformationally controlled molecular switches may find many applications, e.g. in a design of switchable ionophores for membrane transport, or of the triggerable lipid vesicles for drug and gene delivery. The Dean’s Undergraduate Research Award from College of the Pacific, UOP, and the Scholarly/Artistic Activity Grant, and the Eberhardt Research Fellowship from UOP are gratefully acknowledged.