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Synthesis of branched DNA using oxidatively cleavable tritylsulfenyl as a hydroxy protecting group
Kohji Seio1, Takashi Kanamori, Mitsuo Sekine
1Department of Life Science, Tokyo Institute of Technology, Tokyo, Japan.
Abstract:
The application of oxidatively cleavable tritylsulfenyl (TrS) group to the synthesis of branched DNA is described. The TrS protecting group can be removed by treatment with 1 M aqueous iodine, while it is stable toward an oxaziridine-type oxidant. At the same time, the sulfur-oxygen linkage showed sufficient stability under the acidic and basic conditions used in oligonucleotide synthesis. These properties of the TrS group enabled the synthesis of branched DNA using a branched phosphoramidite in which the two hydroxy groups are protected by a 4,4'-dimethoxytrityl (DMTr) group or a TrS group. In this unit, we describe an example of the synthesis of a three-way branched DNA using a branched phosphoramidite.
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