Synthesis of ether-linked oligoribo- and xylonucleosides from 3,5'-ether-linked pseudosaccharides.
First examples of di- and trinucleosides with ribose and xylose stereochemistry having internucleoside ether linkage were synthesized from 3,5'-ether-linked pseudosaccharides. The synthetic protocol involved removal of 1,2-isopropylidene protecting groups from the pseudosaccharides followed by acetylation and a subsequent Vorbruggen transglycosylation with uracil and N-benzoylaminopurine. The synthetic strategy is potentially important for the development of RNA analogues with internucleoside ether linkage.
Sengupta
Jhimli
J
Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Kolkata 700032, India.
Bhattacharjya
Anup
A
D015075:2-Aminopurine / Q000737:chemistry; D000107:Acetylation; D000475:Alkenes / Q000737:chemistry; D004986:Ether / Q000737:chemistry*; D006031:Glycosylation; D008956:Models, Chemical; D009843:Oligoribonucleotides / Q000138:chemical synthesis*; D011134:Polysaccharides / Q000737:chemistry*; D012313:RNA / Q000737:chemistry; D014498:Uracil / Q000737:chemistry; D014994:Xylose / Q000031:analogs & derivatives / Q000138:chemical synthesis*
D000475:Alkenes; D009843:Oligoribonucleotides; D011134:Polysaccharides; D004986:Ether; D015075:2-Aminopurine; D014498:Uracil; D012313:RNA; D014994:Xylose; C013658:propylene