Title

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

Document Type

Poster

Conference Title/Conference Publication

241st National Meeting and Exposition of the American Chemical Society (ACS)

Organization

American Chemical Society (ACS)

Location

Anaheim, CA

Conference Dates

March 27-31, 2011

Date of Presentation

3-29-2011

ISSN

2572-6803

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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