Deoxyribonucleic Acids and Related Compounds. VIII. Solid-Phase Synthesis of Deoxyribooligonucleotides with 3'-Modification by Elongation in the 3'-Direction

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Four dodecanucleotides dATGTTTCCCTCTpOAr (12a), dATGATGTGGTATpOAr (12b), dATGTTGCCCGTTpOAr (12c) and dATGTGTCTGCGGpOAr (12d) having the 3'-(o-chlorophenyl) phosphate moiety have been synthesized on a polymer support by elongation in the 3'-direction. The 5'-succinyl group of N-protected deoxynucleoside 3'-(o-chlorophenyl)-phosphoro-p-anisidates was reacted with the amino group of the aminomethylene derivative of 1% cross linked polystyrene and the 3'-phosphoro-p-anisidate was converted to the phosphodiester by treatment with isoamyl nitrite. The chain was elongated by condensation of the 3'-phosphodiester with 5'-deblocked dinucleotides or trinucleotides having the 3'-(o-chlrophenyl) phosphoro-p-anisidate moiety by using 1-(mesitylenesulfonyl)-3-nitro-1H-1,2,4-triazole as the activating reagent. The reaction was repeated and products were deblocked except for the o-chlorophenyl group on the 3'-phosphate. The overall yields of the dodecamers were 9-16%. The method can be applied to the synthesis of oligonucleotides having nucleoside derivatives at the 3'-end.
社団法人日本薬学会の論文
1984-01-25