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Phosphoramidite building blocks with protected nitroxides for the synthesis of spin-labeled DNA and RNA

  • TEMPO spin labels protected with 2-nitrobenzyloxymethyl groups were attached to the amino residues of three different nucleosides: deoxycytidine, deoxyadenosine, and adenosine. The corresponding phosphoramidites could be incorporated by unmodified standard procedures into four different self-complementary DNA and two RNA oligonucleotides. After photochemical removal of the protective group, elimination of formic aldehyde and spontaneous air oxidation, the nitroxide radicals were regenerated in high yield. The resulting spin-labeled palindromic duplexes could be directly investigated by PELDOR spectroscopy without further purification steps. Spin–spin distances measured by PELDOR correspond well to the values obtained from molecular models.

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Author:Timo WeinrichGND, Eva A. JaumannGND, Ute Scheffer, Thomas F. PrisnerORCiD, Michael GöbelORCiDGND
URN:urn:nbn:de:hebis:30:3-468823
DOI:https://doi.org/10.3762/bjoc.14.133
ISSN:1860-5397
Pubmed Id:https://pubmed.ncbi.nlm.nih.gov/30013683
Parent Title (English):Beilstein journal of organic chemistry
Publisher:Beilstein-Institut zur Förderung der Chemischen Wissenschaften
Place of publication:Frankfurt, Main
Contributor(s):J. S. Dickschat
Document Type:Article
Language:English
Year of Completion:2018
Date of first Publication:2018/06/26
Publishing Institution:Universitätsbibliothek Johann Christian Senckenberg
Release Date:2018/07/31
Tag:EPR; PELDOR; TEMPO; oligonucleotide; photolabile protection
Volume:14
Page Number:7
First Page:1563
Last Page:1569
Note:
This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc)
HeBIS-PPN:43564744X
Institutes:Biochemie, Chemie und Pharmazie / Biochemie und Chemie
Wissenschaftliche Zentren und koordinierte Programme / Zentrum für Biomolekulare Magnetische Resonanz (BMRZ)
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Sammlungen:Universitätspublikationen
Licence (German):License LogoCreative Commons - Namensnennung 4.0

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