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Nucleic Acids Symposium Series 2006 50(1):13-14; doi:10.1093/nass/nrl007
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© 2006 Oxford University Press

Synthesis of 2',4'-BNACOC bearing a purine nucleobase

Yasunori Mitsuoka1, Ryo Ohnishi1, Yoshiyuki Hari1, Satoshi Obika1,2 and Takeshi Imanishi1

1 Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan, 2 PRESTO, JST, 4-1-8 Honcho Kawaguchi, Saitama 332-0012, Japan

Recently, we have synthesized pyrimidine derivatives of 2',4'-BNACOC monomer, the sugar conformation of which was restricted in N-form by a seven-membered bridged structure. The oligonucleotides containing these monomers showed high affinity with complementary single-stranded RNA and significant resistance to nuclease degradation. For an application to antisense methodology, it is important to synthesize 2',4'-BNACOC monomers bearing a purine nucleobase. However, the formation of methyleneoxymethylene (COC) linkage in the purine derivatives failed under the acidic conditions used for the synthesis of 2',4'-BNACOC with pyrimidine nucleobases. After several examinations, we successfully achieved the synthesis of 2',4'-BNACOC monomers bearing a purine nucleobase via the formation of COC linkage using Pummerer-type reaction.


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