Solid Phase Synthesis of Oligodeoxyribonucleotides Utilizing the Phenylthio Group as a Phosphate Protecting Group

Article abstract of DOI:10.1246/bcsj.60.1407

Oligodeoxyribonucleotide synthesis utilizing the phenylthio group as a phosphate protecting group was applied to the solid phase method.The base residues of deoxyguanosine and deoxyadenosine were protected with bis(isobutyryloxy)ethylene (Bibe) and phthaloyl groups to avoid the base modfication and depurination, respectively.A key synthetic intermediate of N²-isobutyryl-N¹,N²-bis(isobutyryloxy)ethylenedeoxyguanosine was prepared in high yield by four-step reaction from deoxyguanosine and used for preparation of the building blocks of deoxyguanosine required for the polymer support synthesis.Two kinds of polymer supports, i.e., 1 percent cross-linked polystyrene and controlled pore glass were chosen.The latter was employed for the synthesis of dodecadeoxyribonucleotides by using an automated DNA synthesizer.