dc.contributor |
Háskóli Íslands |
dc.contributor |
University of Iceland |
dc.contributor.author |
Juliusson, Haraldur Y. |
dc.contributor.author |
Segler, Anna-Lena J. |
dc.contributor.author |
Sigurdsson, Snorri |
dc.date.accessioned |
2020-08-11T15:25:11Z |
dc.date.available |
2020-08-11T15:25:11Z |
dc.date.issued |
2019-06-17 |
dc.identifier.citation |
Juliusson, H. Y., Segler, A. L. J., & Sigurdsson, S. T. (2019). Benzoyl-protected hydroxylamines for improved chemical synthesis of oligonucleotides containing nitroxide spin labels. European Journal of Organic Chemistry, 2019(23), 3799-3805 doi:10.1002/ejoc.201900553 |
dc.identifier.issn |
1434-193X |
dc.identifier.issn |
1099-0690 (eISSN) |
dc.identifier.uri |
https://hdl.handle.net/20.500.11815/1973 |
dc.description |
Post-print (lokagerð höfundar) |
dc.description.abstract |
Oligonucleotides containing nitroxide spin labels, used in biophysical studies of nucleic acids, are frequently prepared by chemical synthesis. However, during the synthesis of spin‐labeled oligonucleotides, the nitroxides are partially reduced to the corresponding amines. Here we report that a benzoylated hydroxylamine can be used as a protected form of the nitroxide to avoid this reduction. The benzoyl group is stable through the oligonucleotide synthesis and is readily removed under standard oligonucleotide deprotection conditions, yielding a hydroxylamine that is oxidized in situ to the nitroxide. This method was used to incorporate the rigid spin labels Ç and Çm into DNA and RNA oligonucleotides, respectively, including a doubly labeled 36‐nucleotide long DNAzyme. Enzymatic digestion of the spin‐labeled oligonucleotides and subsequent HPLC analysis showed that the nitroxides were intact. This protecting group strategy facilitates the high‐yielding synthesis of spin‐labeled DNA and RNA oligonucleotides using the phosphoramidite method. |
dc.description.sponsorship |
The authors acknowledge financial support by the Icelandic Research Fund (141062-051). The authors thank Dr S. Jonsdottir for assistance with collecting analytical data for structural characterization of new compounds and members of the Sigurdsson research group for helpful discussions. |
dc.format.extent |
3799-3805 |
dc.language.iso |
en |
dc.publisher |
Wiley |
dc.relation.ispartofseries |
European Journal of Organic Chemistry;2019(23) |
dc.rights |
info:eu-repo/semantics/openAccess |
dc.subject |
EPR spectroscopy |
dc.subject |
Nitroxides |
dc.subject |
Oligonucleotides |
dc.subject |
Site‐directed spin labeling |
dc.subject |
Litrófsgreining |
dc.subject |
Sameindaerfðafræði |
dc.title |
Benzoyl-Protected Hydroxylamines for Improved Chemical Synthesis of Oligonucleotides Containing Nitroxide Spin Labels |
dc.type |
info:eu-repo/semantics/article |
dcterms.license |
This is the peer reviewed version of the following article: [Juliusson, H. Y., Segler, A. L. J., & Sigurdsson, S. T. (2019). Benzoyl-protected hydroxylamines for improved chemical synthesis of oligonucleotides containing nitroxide spin labels. European Journal of Organic Chemistry, 2019(23), 3799-3805 doi:10.1002/ejoc.201900553], which has been published in final form at https://doi.org/10.1002/ejoc.201900553. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. |
dc.description.version |
Peer reviewed |
dc.identifier.journal |
European Journal of Organic Chemistry |
dc.identifier.doi |
10.1002/ejoc.201900553 |
dc.contributor.department |
Raunvísindadeild (HÍ) |
dc.contributor.department |
Faculty of Physical Sciences (UI) |
dc.contributor.department |
Raunvísindastofnun (HÍ) |
dc.contributor.department |
Science Institute (UI) |
dc.contributor.school |
Verkfræði- og náttúruvísindasvið (HÍ) |
dc.contributor.school |
School of Engineering and Natural Sciences (UI) |