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 Full article

Journal

Journal of Organic Chemistry
ISSN: 0022-3263

Output data

Year: 2012, Volume: 77, Number: 18, Pages: 8016-8027 Pages count : DOI: 10.1021/jo301235j

Authors

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

Affiliations

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 OpenAlex

Published online:	Sep 4, 2012
Published print:	Sep 21, 2012

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

DB	Citing
Web of science	70
Scopus	63
Elibrary	69
OpenAlex	65