Title

pH-Triggered conformational switches based on trans-2-aminocyclohexanol moiety

Document Type

Conference Presentation

Department

Chemistry

Conference Title

241st American Chemical Society (ACS) National Meeting & Exposition

Organization

American Chemical Society (ACS)

Location

Anaheim, CA

Conference Dates

March 27-31, 2011

Date of Presentation

3-29-2011

Abstract

Properly designed trans-2-aminocyclohexanols possess a negative allosteric cooperativity and can serve as powerful conformational pH-triggers. Their protonation leads to a conformational flip due to a strong intramolecular hydrogen bond. This 'impulse' is mechanically transmitted by the cycle to induce a conformational change of a remote site, thus altering its properties. Variation of NR2 groups allows a tuning of the conformational equilibrium, which was studied by NMR. These triggers were used in pH-sensitive lipid vesicles for drug and gene delivery.

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