DNA containing side chains with terminal triple bonds: Base-pair stability and functionalization of alkynylated pyrimidines and 7-deazapurines.
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').
Seela
Frank
F
Laboratorium für Organische und Bioorganische Chemie, Universität Osnabrück, Barbarastrasse 7, D-49069 Osnabrück. Frank.Seela@uni-osnabrueck.de
Sirivolu
Venkata Ramana
VR
D020029:Base Pairing; D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000737:chemistry* / Q000235:genetics; D015394:Molecular Structure; D011743:Pyrimidines / Q000737:chemistry*
D011743:Pyrimidines; D004247:DNA