A new strategy for the synthesis of oligodeoxynucleotides in the phosphoramidite method without base protection via phosphite intermediates.
Deoxyadenosine and deoxycytidine have highly nucleophilic amino groups. Therefore, without base protection, the undesired N-phosphitylations of these amino groups occur in the previous phosphoramidite methods. Now, we report that these N-phosphitylations were considerably suppressed in our new coupling strategy using HOBt as a promoter capable of formation of phosphite-type intermediates.
Ohkubo
Akihiro
A
Department of Life Science, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 226-8501, Japan.
Ezawa
Yusuke
Y
Seio
Kohji
K
Sekine
Mitsuo
M
D000577:Amides / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D017905:Phosphites / Q000737:chemistry*; D010756:Phosphoric Acids / Q000737:chemistry*
D000577:Amides; D009838:Oligodeoxyribonucleotides; D017905:Phosphites; D010756:Phosphoric Acids; C011067:phosphoramidic acid