Synthesis and properties of oligonucleotides containing 4'-selenoribonucleosides.
We report herein the synthesis and properties of oligonucleotides (ONs) containing 4'-selenoribonucleosides. 4'-Selenouridine derivative 1, prepared via the stereoselective seleno-Pummerer reaction, was converted into 4'-selenouridine 9 and -cytidine 10 phosphoramidites. The resulting 4'-selenouridine unit was stable under a standard phosphoramidite protocol including oxidation step and was able to be introduced in ONs (5'-UUUUUU-3', and 5'-UUUUUU-3'). This is the first example of ONs synthesis containing 4'-selenoribonucleosides.
Inagaki
Yusuke
Y
Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-ku, Sapporo 060-0812, Japan.
Minakawa
Noriaki
N
Matsuda
Akira
A
D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012263:Ribonucleosides / Q000737:chemistry*
D009841:Oligonucleotides; D009943:Organophosphorus Compounds; D016566:Organoselenium Compounds; D012263:Ribonucleosides; C434331:phosphoramidite