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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