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pH-Triggered conformational switches based on trans-2-aminocyclohexanol moietyтезисы доклада
- Авторы: Chertkov V.A., Samoshin V.V., Zheng Y., Liu X., Samoshina N.M., Franz A.H., Guo X.
- Сборник: 241st ACS National Meeting
- Тезисы
- Год издания: 2011
- Место издания: Anaheim, California
- Первая страница: 425-ORGN
- Последняя страница: 425-ORGN
- Аннотация: Protonation of trans-3,4-diacetoxy-1-benzylpiperidine leads to dramatic conformational changes: due to a strong intramolecular hydrogen bond, a conformer with axial positions of both acetoxy groups becomes strongly predominant. This conformational flip was studied by 1H NMR. It occurs while pH (pD) of the d4-methanol solution decreases from 6 to 3. As a result of the flip, the separation of acetoxy groups increases drastically thus altering their interactions. For similar structures with substituents designed to perform certain geometry-dependent functions, e.g. as cation chelators or as lipid tails, an incorporated trans-3,4-disubstituted piperidine moiety can serve as a powerful conformational pH-trigger of these functions.
- Добавил в систему: Чертков Вячеслав Алексеевич