3,4-Unsubstituted 2-tert-Butyl-pyrrolidine-1-oxyls with Hydrophilic Functional Groups in the Side Chains

Pyrrolidine nitroxides with four bulky alkyl substituents adjacent to N–O group are known for their high resistance to bioreduction. The 3,4-unsubstituted 2-tert-butyl-2-ethylpyrrolidine-1-oxyls were prepared from the corresponding 2-tert-butyl-1-pyrroline-1-oxides via either the addition of ethinyl...

Descripción completa

Detalles Bibliográficos
Autores principales: Taratayko, Andrey I., Glazachev, Yurii I., Eltsov, Ilia V., Chernyak, Elena I., Kirilyuk, Igor A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8948954/
https://www.ncbi.nlm.nih.gov/pubmed/35335285
http://dx.doi.org/10.3390/molecules27061922
_version_ 1784674777380683776
author Taratayko, Andrey I.
Glazachev, Yurii I.
Eltsov, Ilia V.
Chernyak, Elena I.
Kirilyuk, Igor A.
author_facet Taratayko, Andrey I.
Glazachev, Yurii I.
Eltsov, Ilia V.
Chernyak, Elena I.
Kirilyuk, Igor A.
author_sort Taratayko, Andrey I.
collection PubMed
description Pyrrolidine nitroxides with four bulky alkyl substituents adjacent to N–O group are known for their high resistance to bioreduction. The 3,4-unsubstituted 2-tert-butyl-2-ethylpyrrolidine-1-oxyls were prepared from the corresponding 2-tert-butyl-1-pyrroline-1-oxides via either the addition of ethinylmagnesium bromide with subsequent hydrogenation or via treatment with ethyllithium. The new nitroxides showed excellent stability to reduction with ascorbate with no evidence for additional large hyperfine couplings in the EPR spectra.
format Online
Article
Text
id pubmed-8948954
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-89489542022-03-26 3,4-Unsubstituted 2-tert-Butyl-pyrrolidine-1-oxyls with Hydrophilic Functional Groups in the Side Chains Taratayko, Andrey I. Glazachev, Yurii I. Eltsov, Ilia V. Chernyak, Elena I. Kirilyuk, Igor A. Molecules Article Pyrrolidine nitroxides with four bulky alkyl substituents adjacent to N–O group are known for their high resistance to bioreduction. The 3,4-unsubstituted 2-tert-butyl-2-ethylpyrrolidine-1-oxyls were prepared from the corresponding 2-tert-butyl-1-pyrroline-1-oxides via either the addition of ethinylmagnesium bromide with subsequent hydrogenation or via treatment with ethyllithium. The new nitroxides showed excellent stability to reduction with ascorbate with no evidence for additional large hyperfine couplings in the EPR spectra. MDPI 2022-03-16 /pmc/articles/PMC8948954/ /pubmed/35335285 http://dx.doi.org/10.3390/molecules27061922 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Taratayko, Andrey I.
Glazachev, Yurii I.
Eltsov, Ilia V.
Chernyak, Elena I.
Kirilyuk, Igor A.
3,4-Unsubstituted 2-tert-Butyl-pyrrolidine-1-oxyls with Hydrophilic Functional Groups in the Side Chains
title 3,4-Unsubstituted 2-tert-Butyl-pyrrolidine-1-oxyls with Hydrophilic Functional Groups in the Side Chains
title_full 3,4-Unsubstituted 2-tert-Butyl-pyrrolidine-1-oxyls with Hydrophilic Functional Groups in the Side Chains
title_fullStr 3,4-Unsubstituted 2-tert-Butyl-pyrrolidine-1-oxyls with Hydrophilic Functional Groups in the Side Chains
title_full_unstemmed 3,4-Unsubstituted 2-tert-Butyl-pyrrolidine-1-oxyls with Hydrophilic Functional Groups in the Side Chains
title_short 3,4-Unsubstituted 2-tert-Butyl-pyrrolidine-1-oxyls with Hydrophilic Functional Groups in the Side Chains
title_sort 3,4-unsubstituted 2-tert-butyl-pyrrolidine-1-oxyls with hydrophilic functional groups in the side chains
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8948954/
https://www.ncbi.nlm.nih.gov/pubmed/35335285
http://dx.doi.org/10.3390/molecules27061922
work_keys_str_mv AT tarataykoandreyi 34unsubstituted2tertbutylpyrrolidine1oxylswithhydrophilicfunctionalgroupsinthesidechains
AT glazachevyuriii 34unsubstituted2tertbutylpyrrolidine1oxylswithhydrophilicfunctionalgroupsinthesidechains
AT eltsoviliav 34unsubstituted2tertbutylpyrrolidine1oxylswithhydrophilicfunctionalgroupsinthesidechains
AT chernyakelenai 34unsubstituted2tertbutylpyrrolidine1oxylswithhydrophilicfunctionalgroupsinthesidechains
AT kirilyukigora 34unsubstituted2tertbutylpyrrolidine1oxylswithhydrophilicfunctionalgroupsinthesidechains

Ejemplares similares