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Reduction Resistant and Rigid Nitroxide Spin-Labels for DNA and RNA

Reduction Resistant and Rigid Nitroxide Spin-Labels for DNA and RNA

Title: Reduction Resistant and Rigid Nitroxide Spin-Labels for DNA and RNA
Author: Juliusson, Haraldur Y.
Sigurdsson, Snorri   orcid.org/0000-0003-2492-1456
Date: 2020-02-27
Language: English
Scope: 4036-4046
University/Institute: Háskóli Íslands
University of Iceland
School: Verkfræði- og náttúruvísindasvið (HÍ)
School of Engineering and Natural Sciences (UI)
Department: Raunvísindadeild (HÍ)
Faculty of Physical Sciences (UI)
Raunvísindastofnun (HÍ)
Science Institute (UI)
Series: The Journal of Organic Chemistry;85(6)
ISSN: 0022-3263
1520-6904 (eISSN)
DOI: 10.1021/acs.joc.9b02988
Subject: Redox reactions; Genetics; EPR spectroscopy; Quantum mechanics; Biopolymers; Erfðafræði; Litrófsgreining; Skammtafræði
URI: https://hdl.handle.net/20.500.11815/1977

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Juliusson, H. Y., & Sigurdsson, S. T. (2020). Reduction resistant and rigid nitroxide spin-labels for DNA and RNA. Journal of Organic Chemistry, 85(6), 4036-4046 doi: 10.1021/acs.joc.9b02988


Electron paramagnetic resonance (EPR) spectroscopy, coupled with site-directed spin labeling (SDSL), is a useful method for studying conformational changes of biomolecules in cells. To employ in-cell EPR using nitroxide-based spin labels, the structure of the nitroxides must confer reduction resistance to withstand the reductive environment within cells. Here, we report the synthesis of two new spin labels, EÇ and EÇm, both of which possess the rigidity and the reduction resistance needed for extracting detailed structural information by EPR spectroscopy. EÇ and EÇm were incorporated into DNA and RNA, respectively, by oligonucleotide synthesis. Both labels were shown to be nonperturbing of the duplex structure. The partial reduction of EÇm during RNA synthesis was circumvented by the protection of the nitroxide as a benzoylated hydroxylamine.


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This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by t he publisher. To access the final edited and published work see [insert ACS Articles on Request author-directed link to Published Work, see http://pubs.acs.org/page/policy/articlesonrequest/index.html].

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