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-complem...
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Beilstein-Institut
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.14.133 |
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doaj-455c1588d27644cfac493d56c4b31a862021-02-02T04:39:10ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-06-011411563156910.3762/bjoc.14.1331860-5397-14-133Phosphoramidite building blocks with protected nitroxides for the synthesis of spin-labeled DNA and RNATimo Weinrich0Eva A. Jaumann1Ute M. Scheffer2Thomas F. Prisner3Michael W. Göbel4Institute of Organic Chemistry and Chemical Biology, Goethe University Frankfurt, Max-von-Laue-Str. 7, D-60438 Frankfurt am Main, GermanyInstitute of Physical and Theoretical Chemistry, Goethe University Frankfurt, Max-von-Laue-Str. 7, D-60438 Frankfurt am Main, GermanyInstitute of Organic Chemistry and Chemical Biology, Goethe University Frankfurt, Max-von-Laue-Str. 7, D-60438 Frankfurt am Main, GermanyInstitute of Physical and Theoretical Chemistry, Goethe University Frankfurt, Max-von-Laue-Str. 7, D-60438 Frankfurt am Main, GermanyInstitute of Organic Chemistry and Chemical Biology, Goethe University Frankfurt, Max-von-Laue-Str. 7, D-60438 Frankfurt am Main, GermanyTEMPO 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.https://doi.org/10.3762/bjoc.14.133EPRoligonucleotidePELDORphotolabile protectionTEMPO |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Timo Weinrich Eva A. Jaumann Ute M. Scheffer Thomas F. Prisner Michael W. Göbel |
| spellingShingle |
Timo Weinrich Eva A. Jaumann Ute M. Scheffer Thomas F. Prisner Michael W. Göbel Phosphoramidite building blocks with protected nitroxides for the synthesis of spin-labeled DNA and RNA Beilstein Journal of Organic Chemistry EPR oligonucleotide PELDOR photolabile protection TEMPO |
| author_facet |
Timo Weinrich Eva A. Jaumann Ute M. Scheffer Thomas F. Prisner Michael W. Göbel |
| author_sort |
Timo Weinrich |
| title |
Phosphoramidite building blocks with protected nitroxides for the synthesis of spin-labeled DNA and RNA |
| title_short |
Phosphoramidite building blocks with protected nitroxides for the synthesis of spin-labeled DNA and RNA |
| title_full |
Phosphoramidite building blocks with protected nitroxides for the synthesis of spin-labeled DNA and RNA |
| title_fullStr |
Phosphoramidite building blocks with protected nitroxides for the synthesis of spin-labeled DNA and RNA |
| title_full_unstemmed |
Phosphoramidite building blocks with protected nitroxides for the synthesis of spin-labeled DNA and RNA |
| title_sort |
phosphoramidite building blocks with protected nitroxides for the synthesis of spin-labeled dna and rna |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2018-06-01 |
| description |
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. |
| topic |
EPR oligonucleotide PELDOR photolabile protection TEMPO |
| url |
https://doi.org/10.3762/bjoc.14.133 |
| work_keys_str_mv |
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