KFU. Card publication. 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

Form of presentation

Articles in international journals and collections

Year of publication

2016

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Authors, employees of KFU

Latypova Liliya Zinnurovna, author

Authors, students KFU

Smirnov Ivan Sergeevich, author

Bibliographic description in the original language

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.

Annotation

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.

Keywords

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

The name of the journal

BioNanoScience

URL

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

Please use this ID to quote from or refer to the card

https://repository.kpfu.ru/eng/?p_id=135601&p_lang=2

Full metadata record

Field DC	Value	Language
dc.contributor.author	Latypova Liliya Zinnurovna	ru_RU
dc.contributor.author	Smirnov Ivan Sergeevich	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/eng/?p_id=135601&p_lang=2	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	Articles in international journals and collections	ru_RU