Synthesis of 2,5-Bis(spirocyclohexane)-Substituted Nitroxides of Pyrroline and Pyrrolidine Series, Including Thiol-Specific Spin Label: An Analogue of MTSSL with Long Relaxation Time

Synthesis of 2,5-Bis(spirocyclohexane)-Substituted Nitroxides of Pyrroline and Pyrrolidine Series, Including Thiol-Specific Spin Label: An Analogue of MTSSL with Long Relaxation Time Научная публикация

Журнал

Journal of Organic Chemistry
ISSN: 0022-3263

Вых. Данные

Год: 2012, Том: 77, Номер: 18, Страницы: 8016-8027 Страниц : DOI: 10.1021/jo301235j

Авторы

Kirilyuk Igor A. ¹ , Polienko Yuliya F. ¹ , Krumkacheva Olesya A. ² , Strizhakov Rodion K. ² , Gatilov Yurii V. ¹ , Grigor'ev Igor A. ¹ , Bagryanskaya Elena G. ^1,2

Организации

1	(Данные Web of science) RAS, NN Vorozhtsov Novosibirsk Inst Organ Chem Sb, Novosibirsk 630090, Russia
2	(Данные Web of science) RAS, Int Tomog Ctr SB, Novosibirsk 630090, Russia

The nitroxides of 7-azadispiro[5.1.5.2]-pentadecane and 7-azadispiro[5.1.5.2]pentadeca-14-ene series have been prepared, including thiol-specific methane thiosulfonate spin label for site-directed spin labeling. The effect of spirocyclohexane moieties on chemical and spectral properties has been studied. The obtained temperature dependencies of electron spin relaxation parameters demonstrate that new nitroxides may be suitable for PELDOR distance measurements at 80-120 K. Moreover, the new nitroxides demonstrated much higher stability toward reduction by ascorbate than spirocyclohexane-substituted nitroxides of piperidine series and showed 1.3-3.14 times lower reduction rates compared to corresponding 2,2,5,5-tetramethyl nitroxides.

Kirilyuk I.A. , Polienko Y.F. , Krumkacheva O.A. , Strizhakov R.K. , Gatilov Y.V. , Grigor'ev I.A. , Bagryanskaya E.G.
Synthesis of 2,5-Bis(spirocyclohexane)-Substituted Nitroxides of Pyrroline and Pyrrolidine Series, Including Thiol-Specific Spin Label: An Analogue of MTSSL with Long Relaxation Time
Journal of Organic Chemistry. 2012. V.77. N18. P.8016-8027. DOI: 10.1021/jo301235j WOS Scopus РИНЦ

Опубликована online:	4 сент. 2012 г.
Опубликована в печати:	21 сент. 2012 г.

Web of science	WOS:000308957700024
Scopus	2-s2.0-84867705933
РИНЦ	20496930
OpenAlex	W2328326144