DNA containing side chains with terminal triple bonds: Base-pair stability and functionalization of alkynylated pyrimidines and 7-deazapurines
Autor(en): | Seela, Frank Sirivolu, Venkata Ramana |
Stichwörter: | ALKYNES; Biochemistry & Molecular Biology; Chemistry; Chemistry, Multidisciplinary; DUPLEX STABILITY; OLIGODEOXYNUCLEOTIDES; OLIGONUCLEOTIDES | Erscheinungsdatum: | 2006 | Herausgeber: | WILEY-V C H VERLAG GMBH | Journal: | CHEMISTRY & BIODIVERSITY | Volumen: | 3 | Ausgabe: | 5 | Startseite: | 509 | Seitenende: | 514 | Zusammenfassung: | The synthesis of a series of oligonucleotides containing 5-substituted pyrimidines as well as 7-substituted 7-deazapurines bearing diyne groups with terminal triple bonds is reported. The modified nucleosides were prepared from the corresponding iodo nucleosides and diynes by the Sonogashira cross-coupling reaction. They were converted into phosphoramidites and employed in solid-phase synthesis of oligonucleotides. The effect of the diyne modifications on the duplex stability was investigated. The modified nucleosides were used for further functionalization using the protocol of Huisgen-Sharpless [2 3] cycloaddition ('click chemistry'). |
ISSN: | 16121872 | DOI: | 10.1002/cbdv.200690054 |
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