Novel Dioxane and Morpholino Nucleotide Analogues: Syntheses and RNA‐Hybridization Properties
| Autor: | Kerstin Jahn-Hofmann, Sabine Scheidler, Armin Hofmeister, Arne Krack, Michael Kurz, Armin Müller |
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| Rok vydání: | 2020 |
| Předmět: |
Stereochemistry
Oligonucleotide synthesis 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry Morpholinos Dioxanes chemistry.chemical_compound Morpholine Transition Temperature Nucleotide Molecular Biology RNA Double-Stranded chemistry.chemical_classification 010405 organic chemistry Oligonucleotide Organic Chemistry Diastereomer Nucleic Acid Hybridization RNA Stereoisomerism 0104 chemical sciences chemistry Molecular Medicine Chirality (chemistry) Thymidine |
| Zdroj: | ChemBioChem. 22:1072-1078 |
| ISSN: | 1439-7633 1439-4227 |
| Popis: | A novel class of nucleotide analogues with a dioxane ring as central scaffold has been developed. Synthetic routes in two diastereomeric series were realized, and the final thymidine analogues were synthesized with common functionalities for the automated oligonucleotide synthesis. The chemical space of the initially derived nucleotides was expanded by changing the central dioxane to analogous morpholine derivatives. This opens up the possibility for further derivatization by attaching different substituents at the morpholine nitrogen. The novel nucleotide building blocks were incorporated into double-stranded RNA sequences, and their hybridization properties investigated by melting-temperature analysis. Both scaffolds, dioxanes and morpholines, had an equal impact on double-strand stability, but Tm values differed depending on the chirality in the six-membered ring. |
| Databáze: | OpenAIRE |
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