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Conformational Selection in Anion Recognition: cGMP-Selective Binding by a Naphthalimide-Functionalized Amido-Amine Macrocycleстатья
Статья опубликована в высокорейтинговом журнале
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 8 сентября 2021 г.
- Авторы: Oshchepkov Aleksandr S., Shumilova Tatiana A., Zerson Mario, Magerle Robert, Khrustalev Victor N., Kataev Evgeny A.
- Журнал: Journal of Organic Chemistry
- Том: 84
- Номер: 14
- Год издания: 2019
- Издательство: American Chemical Society
- Местоположение издательства: United States
- Первая страница: 9034
- Последняя страница: 9043
- DOI: 10.1021/acs.joc.9b00947
- Аннотация: Amido-amine macrocycles with two and four naphthalimide dyes were designed to bind nucleoside monophosphates and oligonucleotides in an aqueous buffered solution. Anion-templated synthesis was used to direct the macrocyclization reaction to the [2+2] product, while high dilution conditions favored the formation of the [4+4] macrocycle with an unprecedented geometry, as revealed from the X-ray analysis. The [2+2] product was found to exhibit a remarkable binding strength and fluorescence response for cyclic guanosine monophosphate (cGMP) in an aqueous solution. To our knowledge, this is the first synthetic receptor for cGMP, which also demonstrates a high preference to bind guanine-rich sequences accomplished by a strong fluorescence quenching. The receptor conformation is very sensitive to the guest structure in an aqueous solution, thus modeling the adaptive behavior of proteins. The study of synthetic systems with a detectable conformational equilibrium represents a great potential for understanding highly specific and tightly regulated interactions in biological systems.
- Добавил в систему: Ощепков Александр Сергеевич