The impact of an extended nucleobase-2′-deoxyribose linker in the biophysical and biological properties of oligonucleotides
Interest in artificial DNA mimetics has been triggered by the widespread applications of nucleic acids as they are useful tools for modulation of the biophysical and biological properties of oligonucleotides. In this article, we describe the synthesis and properties of a novel thymine derivative (T*...
| Main Authors: | , , , , , , , |
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| Format: | Journal article |
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Royal Society of Chemistry
2017
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| _version_ | 1826283126489350144 |
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| author | Carnero, A Pérez-Rentero, S Alagia, A Aviñó, A Sanghvi, Y Fernández, S Ferrero, M Eritja, R |
| author_facet | Carnero, A Pérez-Rentero, S Alagia, A Aviñó, A Sanghvi, Y Fernández, S Ferrero, M Eritja, R |
| author_sort | Carnero, A |
| collection | OXFORD |
| description | Interest in artificial DNA mimetics has been triggered by the widespread applications of nucleic acids as they are useful tools for modulation of the biophysical and biological properties of oligonucleotides. In this article, we describe the synthesis and properties of a novel thymine derivative (T*) containing an extended linker between the thymine nucleobase and the 2′-deoxyribose moiety. The modified 2′-deoxyribosyl derivative was prepared via coupling of a functionalized nucleobase to the amino group of 1-aminomethyl-2-deoxyribose, which was synthesized starting from an easily accessible cyano sugar available on a large-scale. Corresponding phosphoramidite and succinyl derivatives have also been incorporated into oligonucleotides at predetermined sites and defined internucleotidic motifs using the solid-phase synthesis approach. This derivative pairs equally well with adenine and guanine and it can be safely introduced at the 3′-end of the siRNAs to generate potent inhibitors of gene expression by the RNA interference mechanism. |
| first_indexed | 2024-03-07T00:54:14Z |
| format | Journal article |
| id | oxford-uuid:8779e627-f1ee-4ab8-8b23-015eec0759a4 |
| institution | University of Oxford |
| last_indexed | 2024-03-07T00:54:14Z |
| publishDate | 2017 |
| publisher | Royal Society of Chemistry |
| record_format | dspace |
| spelling | oxford-uuid:8779e627-f1ee-4ab8-8b23-015eec0759a42022-03-26T22:10:57ZThe impact of an extended nucleobase-2′-deoxyribose linker in the biophysical and biological properties of oligonucleotidesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:8779e627-f1ee-4ab8-8b23-015eec0759a4Symplectic Elements at OxfordRoyal Society of Chemistry2017Carnero, APérez-Rentero, SAlagia, AAviñó, ASanghvi, YFernández, SFerrero, MEritja, RInterest in artificial DNA mimetics has been triggered by the widespread applications of nucleic acids as they are useful tools for modulation of the biophysical and biological properties of oligonucleotides. In this article, we describe the synthesis and properties of a novel thymine derivative (T*) containing an extended linker between the thymine nucleobase and the 2′-deoxyribose moiety. The modified 2′-deoxyribosyl derivative was prepared via coupling of a functionalized nucleobase to the amino group of 1-aminomethyl-2-deoxyribose, which was synthesized starting from an easily accessible cyano sugar available on a large-scale. Corresponding phosphoramidite and succinyl derivatives have also been incorporated into oligonucleotides at predetermined sites and defined internucleotidic motifs using the solid-phase synthesis approach. This derivative pairs equally well with adenine and guanine and it can be safely introduced at the 3′-end of the siRNAs to generate potent inhibitors of gene expression by the RNA interference mechanism. |
| spellingShingle | Carnero, A Pérez-Rentero, S Alagia, A Aviñó, A Sanghvi, Y Fernández, S Ferrero, M Eritja, R The impact of an extended nucleobase-2′-deoxyribose linker in the biophysical and biological properties of oligonucleotides |
| title | The impact of an extended nucleobase-2′-deoxyribose linker in the biophysical and biological properties of oligonucleotides |
| title_full | The impact of an extended nucleobase-2′-deoxyribose linker in the biophysical and biological properties of oligonucleotides |
| title_fullStr | The impact of an extended nucleobase-2′-deoxyribose linker in the biophysical and biological properties of oligonucleotides |
| title_full_unstemmed | The impact of an extended nucleobase-2′-deoxyribose linker in the biophysical and biological properties of oligonucleotides |
| title_short | The impact of an extended nucleobase-2′-deoxyribose linker in the biophysical and biological properties of oligonucleotides |
| title_sort | impact of an extended nucleobase 2 deoxyribose linker in the biophysical and biological properties of oligonucleotides |
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