5'-Levulinyl and 2'-tetrahydrofuranyl protection for the synthesis of oligoribonucleotides by the phosphoramidite approach.
The levulinyl group has been employed for protection of the 5'-hydroxyl group in the synthesis of oligoribonucleotides by the phosphoramidite approach, using the acid-labile 2'-tetrahydro-furanyl group. The hydrazine treatment was performed for 10 minutes in order to remove the levulinyl group on controlled pore glass. Four decaribonucleotides (AAAAAAAAAU, GGGGGGGGGU, CCCCCCCCCU and UUUUUUUUUU) and a heneicosamer (GCCUAGCUGAUGAAGGGUGAU) were prepared with an automatic synthesizer in good yields.
Iwai
S
S
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.
Ohtsuka
E
E
D000622:Aminolevulinic Acid; D001482:Base Composition; D001483:Base Sequence; D005663:Furans; D006834:Hydrazines; D007982:Levulinic Acids; D015345:Oligonucleotide Probes / Q000138:chemical synthesis / Q000302:isolation & purification; D009843:Oligoribonucleotides / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000302:isolation & purification; D009943:Organophosphorus Compounds; D013777:Tetrazoles
D005663:Furans; D006834:Hydrazines; D007982:Levulinic Acids; D015345:Oligonucleotide Probes; D009843:Oligoribonucleotides; D009943:Organophosphorus Compounds; D013777:Tetrazoles; C029424:hydrazine; C049676:diisopropyl phosphoramidite; D000622:Aminolevulinic Acid