1R,5S,7S,8R,12S,13S)-12,13-Dihydroxy-1,8-bis(hydroxymethyl)-6-azadispiro[4.1.4.2]tridecane-6-oxyl - a Chiral Hydrophilic Dispirocyclic Radical with High Stability to Reduction

1R,5S,7S,8R,12S,13S)-12,13-Dihydroxy-1,8-bis(hydroxymethyl)-6-azadispiro[4.1.4.2]tridecane-6-oxyl - a Chiral Hydrophilic Dispirocyclic Radical with High Stability to Reduction Научная публикация

Журнал

CHEMISTRY FOR SUSTAINABLE DEVELOPMENT
ISSN: 1023-8603

Вых. Данные

Год: 2024, Том: 32, Номер: 4, Страницы: 555-565 Страниц : 11 DOI: 10.15372/CSD2024588

Ключевые слова

6-azadispiro[4.1.4.2]tridecane, pyrrolidine nitroxide, hindered nitroxide, spin relaxation

Авторы

KHOROSHUNOVA YU.V. ¹ , MOROZOV D.A. ¹ , RYBALOVA T.V. ¹ , TRAKHININA S.YU. ^1,2 , ASANBAEVA N.B. ¹ , SOTNIKOVA YU.S. ¹ , KIRILYUK I.A. ¹

Организации

1	Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
2	Novosibirsk State University

Информация о финансировании (1)

Российский Научный Фонд

23-23-00617

Modern trends in the development of structural biology make it relevant to study the structure of biomolecules under the conditions close to natural, i.e., directly in a living cell and at temperatures close to physiological ones. One of the promising technologies that allows approaching this ideal is the targeted introduction of spin labels (for example, nitroxides), followed by investigation using pulsed electron paramagnetic resonance (EPR). Today, the greatest stability in living systems is demonstrated by sterically hindered nitroxyl radicals of the pyrrolidine series with four ethyl groups at a paramagnetic centre, but their relaxation characteristics do not allow measurements by pulsed ESR methods at a temperature above 80 K. Nitroxides with spirocycloalkane fragments surrounding the nitroxyl group are suitable for measurements at higher temperatures, but they are rapidly reduced by the components of living systems. Pyrrolidine nitroxides with two spiro-(2-hydroxymethyl)cyclopentane moieties combine high resistance to reduction with high spin relaxation times at a temperature of 120 K and above. In this work, a hydrophilic chiral radical of this series - (1 R ,5 S ,7 S ,8 R ,12 S ,13 S )-12,13-dihydroxy-1,8-bis(hydroxymethyl)-6-azadispiro[4.1.4.2]tridecane-6-oxyl was obtained and characterised by us for the first time.

KHOROSHUNOVA Y.V. , MOROZOV D.A. , RYBALOVA T.V. , TRAKHININA S.Y. , ASANBAEVA N.B. , SOTNIKOVA Y.S. , KIRILYUK I.A.
1R,5S,7S,8R,12S,13S)-12,13-Dihydroxy-1,8-bis(hydroxymethyl)-6-azadispiro[4.1.4.2]tridecane-6-oxyl - a Chiral Hydrophilic Dispirocyclic Radical with High Stability to Reduction
CHEMISTRY FOR SUSTAINABLE DEVELOPMENT. 2024. V.32. N4. P.555-565. DOI: 10.15372/CSD2024588

ХОРОШУНОВА Ю.В. , МОРОЗОВ Д.А. , РЫБАЛОВА Т.В. , ТРАХИНИНА С.Ю. , АСАНБАЕВА Н.Б. , СОТНИКОВА Ю.С. , КИРИЛЮК И.А.
1R,5S,7S,8R,12S,13S)-12,13-Дигидрокси-1,8-бис(гидроксиметил)-6-азадиспиро[4.1.4.2]тридекан-6-оксил - хиральный гидрофильный диспироциклический радикал с высокой устойчивостью к восстановлению
ХИМИЯ В ИНТЕРЕСАХ УСТОЙЧИВОГО РАЗВИТИЯ. 2024. Т.32. №4. С.555-565. DOI: 10.15372/khur2024588

Поступила в редакцию:	31 мая 2024 г.
Принята к публикации:	22 июл. 2024 г.

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