Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
2‐Butyl‐2‐tert‐butyl‐5,5‐diethylpyrrolidine‐1‐oxyls : Synthesis and properties. / Zhurko, Irina F.; Dobrynin, Sergey; Gorodetskii, Artem A. и др.
в: Molecules, Том 25, № 4, 845, 14.02.2020.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - 2‐Butyl‐2‐tert‐butyl‐5,5‐diethylpyrrolidine‐1‐oxyls
T2 - Synthesis and properties
AU - Zhurko, Irina F.
AU - Dobrynin, Sergey
AU - Gorodetskii, Artem A.
AU - Glazachev, Yuri I.
AU - Rybalova, Tatyana V.
AU - Chernyak, Elena I.
AU - Asanbaeva, Nargiz
AU - Bagryanskaya, Elena G.
AU - Kirilyuk, Igor A.
N1 - Publisher Copyright: © 2020 by the authors. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.
PY - 2020/2/14
Y1 - 2020/2/14
N2 - Nitroxides are broadly used as molecular probes and labels in biophysics, structural biology, and biomedical research. Resistance of a nitroxide group bearing an unpaired electron to chemical reduction with low-molecular-weight antioxidants and enzymatic systems is of critical importance for these applications. The redox properties of nitroxides are known to depend on the ring size (for cyclic nitroxides) and electronic and steric effects of the substituents. Here, two highly strained nitroxides, 5-(tert-butyl)-5-butyl-2,2-diethyl-3-hydroxypyrrolidin-1-oxyl (4) and 2-(tert-butyl)-2-butyl-5,5-diethyl-3,4-bis(hydroxymethyl)pyrrolidin-1-oxyl (5), were prepared via a reaction of the corresponding 2-tert-butyl-1-pyrroline 1-oxides with butyllithium. Thermal stability and kinetics of reduction of the new nitroxides by ascorbic acid were studied. Nitroxide 5 showed the highest resistance to reduction.
AB - Nitroxides are broadly used as molecular probes and labels in biophysics, structural biology, and biomedical research. Resistance of a nitroxide group bearing an unpaired electron to chemical reduction with low-molecular-weight antioxidants and enzymatic systems is of critical importance for these applications. The redox properties of nitroxides are known to depend on the ring size (for cyclic nitroxides) and electronic and steric effects of the substituents. Here, two highly strained nitroxides, 5-(tert-butyl)-5-butyl-2,2-diethyl-3-hydroxypyrrolidin-1-oxyl (4) and 2-(tert-butyl)-2-butyl-5,5-diethyl-3,4-bis(hydroxymethyl)pyrrolidin-1-oxyl (5), were prepared via a reaction of the corresponding 2-tert-butyl-1-pyrroline 1-oxides with butyllithium. Thermal stability and kinetics of reduction of the new nitroxides by ascorbic acid were studied. Nitroxide 5 showed the highest resistance to reduction.
KW - 1,3-dipolar cycloaddition reaction
KW - EPR
KW - Nitrones
KW - Nitroxides
KW - Organolithium compounds
KW - Reduction kinetics
KW - Spin probes
KW - NITROXIDE
KW - reduction kinetics
KW - nitroxides
KW - 2-SUBSTITUTED 5,5-DIMETHYL-4-OXO-1-PYRROLINE-1-OXIDES
KW - PYRROLINE
KW - organolithium compounds
KW - spin probes
KW - ALKOXYAMINES
KW - REDUCTION
KW - nitrones
KW - RADICALS
KW - PHOTOLYSIS
KW - DERIVATIVES
KW - EPR SPECTROSCOPY
KW - IMIDAZOLIDINE
UR - http://www.scopus.com/inward/record.url?scp=85079610677&partnerID=8YFLogxK
U2 - 10.3390/molecules25040845
DO - 10.3390/molecules25040845
M3 - Article
C2 - 32075085
AN - SCOPUS:85079610677
VL - 25
JO - Molecules
JF - Molecules
SN - 1420-3049
IS - 4
M1 - 845
ER -
ID: 23594367