КФУ. Карточка публикации. Unrecognized cycloaddition reactions of N-alkyl-α,β-unsaturated imines occurring in biosystems and their biological roles

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UNRECOGNIZED CYCLOADDITION REACTIONS OF N-ALKYL-α,β-UNSATURATED IMINES OCCURRING IN BIOSYSTEMS AND THEIR BIOLOGICAL ROLES

Форма представления

Статьи в зарубежных журналах и сборниках

Год публикации

2016

Язык

английский

Авторы, сотрудники КФУ

Латыпова Лилия Зиннуровна, автор

Авторы, студенты КФУ

Смирнов Иван Сергеевич, автор

Библиографическое описание на языке оригинала

Pradipta A. R. Unrecognized cycloaddition reactions of N-alkyl-α,β-unsaturated imines occurring in biosystems and their biological roles / A. R. Pradipta, A. Tsutsui, L. Latypova, D. Chulakova, I. Smirnov, A. Kurbangalieva, K. Tanaka // BioNanoSci. - 2016. - V. 6. – P. 364–367.

Аннотация

Despite being fundamentally ubiquitous and important species in organic and bioorganic chemistry, the reactivities of N-alkyl-α,β-unsaturated imines have not been thoroughly explored due to their instability. Here, we describe novel reactivities of N-alkyl-α,β-unsaturated imines, which derived from α,β-unsaturated aldehydes (e.g., unsubstituted or substituted acrolein), alkylamines (e.g., amino-alcohols or diamines), and formaldehyde to produce 1,5-diazacyclooctanes, hexahydropyrimidines, and 1,3,5-triazacyclooctanes via formal [4 + 4], [4 + 2], and [4 + 2 + 2] cycloadditions in a stereocontrolled manner. We then also synthetically demonstrated that reaction between acrolein and biogenic amines (e.g., polyamines, noradrenaline, sphingosine), which ubiquitously exist in biosystems, proceed smoothly to give the corresponding 1,5-diazacyclooctanes. Finally, we also examined biological functions of the cycloaddition products and revealed for the first time their roles in oxidative stress.

Ключевые слова

N-Alkyl-α,β-unsaturated imine, imino cycloaddition, 1,5-diazacyclooctane, hexahydropyrimidine, 1,3,5-triazacyclooctane

Название журнала

BioNanoScience

URL

http://link.springer.com/article/10.1007/s12668-016-0236-7

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https://repository.kpfu.ru/?p_id=135601

Полная запись метаданных

Поле DC	Значение	Язык
dc.contributor.author	Латыпова Лилия Зиннуровна	ru_RU
dc.contributor.author	Смирнов Иван Сергеевич	ru_RU
dc.date.accessioned	2016-01-01T00:00:00Z	ru_RU
dc.date.available	2016-01-01T00:00:00Z	ru_RU
dc.date.issued	2016	ru_RU
dc.identifier.citation	Pradipta A. R. Unrecognized cycloaddition reactions of N-alkyl-α,β-unsaturated imines occurring in biosystems and their biological roles / A. R. Pradipta, A. Tsutsui, L. Latypova, D. Chulakova, I. Smirnov, A. Kurbangalieva, K. Tanaka // BioNanoSci. - 2016. - V. 6. – P. 364–367.	ru_RU
dc.identifier.uri	https://repository.kpfu.ru/?p_id=135601	ru_RU
dc.description.abstract	BioNanoScience	ru_RU
dc.description.abstract	Despite being fundamentally ubiquitous and important species in organic and bioorganic chemistry, the reactivities of N-alkyl-α,β-unsaturated imines have not been thoroughly explored due to their instability. Here, we describe novel reactivities of N-alkyl-α,β-unsaturated imines, which derived from α,β-unsaturated aldehydes (e.g., unsubstituted or substituted acrolein), alkylamines (e.g., amino-alcohols or diamines), and formaldehyde to produce 1,5-diazacyclooctanes, hexahydropyrimidines, and 1,3,5-triazacyclooctanes via formal [4 + 4], [4 + 2], and [4 + 2 + 2] cycloadditions in a stereocontrolled manner. We then also synthetically demonstrated that reaction between acrolein and biogenic amines (e.g., polyamines, noradrenaline, sphingosine), which ubiquitously exist in biosystems, proceed smoothly to give the corresponding 1,5-diazacyclooctanes. Finally, we also examined biological functions of the cycloaddition products and revealed for the first time their roles in oxidative stress.	ru_RU
dc.language.iso	ru	ru_RU
dc.subject	N-Alkyl-α	ru_RU
dc.subject	β-unsaturated imine	ru_RU
dc.subject	imino cycloaddition	ru_RU
dc.subject	1	ru_RU
dc.subject	5-diazacyclooctane	ru_RU
dc.subject	hexahydropyrimidine	ru_RU
dc.subject	1	ru_RU
dc.subject	3	ru_RU
dc.subject	5-triazacyclooctane	ru_RU
dc.title	Unrecognized cycloaddition reactions of N-alkyl-α,β-unsaturated imines occurring in biosystems and their biological roles	ru_RU
dc.type	Статьи в зарубежных журналах и сборниках	ru_RU