%0 Journal Article
%T Synthesis of Oligodeoxynucleotides Using Fully Protected Deoxynucleoside 3กไ-Phosphoramidite Building Blocks and Base Recognition of Oligodeoxynucleotides Incorporating N3-Cyano-Ethylthymine
%A Hirosuke Tsunoda
%A Tomomi Kudo
%A Akihiro Ohkubo
%A Kohji Seio
%A Mitsuo Sekine
%J Molecules
%D 2010
%I MDPI AG
%R 10.3390/molecules15117509
%X Oligodeoxynucleotide (ODN) synthesis, which avoids the formation of side products, is of great importance to biochemistry-based technology development. One side reaction of ODN synthesis is the cyanoethylation of the nucleobases. We suppressed this reaction by synthesizing ODNs using fully protected deoxynucleoside 3กไ-phosphoramidite building blocks, where the remaining reactive nucleobase residues were completely protected with acyl-, diacyl-, and acyl-oxyethylene-type groups. The detailed analysis of cyanoethylation at the nucleobase site showed that N3-protection of the thymine base efficiently suppressed the Michael addition of acrylonitrile. An ODN incorporating N3-cyanoethylthymine was synthesized using the phosphoramidite method, and primer extension reactions involving this ODN template were examined. As a result, the modified thymine produced has been proven to serve as a chain terminator.
%K protecting group
%K oligodeoxynucleotide synthesis
%K cyanoethylation
%U http://www.mdpi.com/1420-3049/15/11/7509