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