Chemoselective Modification of Vinyl DNA by Triazolinediones
| Autor: | Anu Naik, Anna Bujalska, Therese Triemer, Jawad Alzeer, Nathan W. Luedtke |
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| Přispěvatelé: | University of Zurich, Luedtke, Nathan W |
| Rok vydání: | 2017 |
| Předmět: |
10120 Department of Chemistry
1503 Catalysis Context (language use) 1600 General Chemistry 010402 general chemistry 01 natural sciences Catalysis Nucleobase 540 Chemistry Organic chemistry chemistry.chemical_classification Bioconjugation Molecular Structure 010405 organic chemistry Oligonucleotide Alkene General Chemistry General Medicine DNA Triazoles Combinatorial chemistry Cycloaddition 0104 chemical sciences chemistry Nucleic acid Click chemistry |
| Zdroj: | Angewandte Chemie (International ed. in English). 56(36) |
| ISSN: | 1521-3773 |
| Popis: | A new method for the post-synthetic modification of nucleic acids was developed that involves mixing a phenyl triazolinedione (PTAD) derivative with DNA containing a vinyl nucleobase. The resulting reactions proceeded through step-wise mechanisms, giving either a formal [4+2] cycloaddition product, or, depending on the context of nucleobase, PTAD addition along with solvent trapping to give a secondary alcohol in water. Catalyst-free addition between PTAD and the terminal alkene of 5-vinyl-2'-deoxyuridine (VdU) was exceptionally fast, with a second-order rate constant of 2×103 m-1 s-1 . PTAD derivatives selectively reacted with VdU-containing oligonucleotides in a conformation-selective manner, with higher yields observed for G-quadruplex versus duplex DNA. These results demonstrate a new strategy for copper-free bioconjugation of DNA that can potentially be used to probe nucleic acid conformations in cells. |
| Databáze: | OpenAIRE |
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