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A new strategy for the synthesis of oligodeoxynucleotides directed towards perfect O-selective internucleotidic bond formation without base protection |
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| Authors: | Akihiro Ohkubo Kohji Seio Mitsuo Sekine |
| Affiliation: | a Department of Life Science, Tokyo Institute of Technology, Nagatsuta, Mirdoriku, Yokohama 226-8501, Japan b Division of Collaborative Research for Bioscience and Biotechnology, Frontier Collaborative Research Center, Nagatsuta, Mirdoriku, Yokohama 226-8501, Japan c CREST, JST (Japan Science and Technology Corporation), Nagatsuta, Mirdoriku, Yokohama 226-8501, Japan |
| Abstract: | Deoxyadenosine and deoxycytidine have nucleophilic amino groups so that the undesired N-phosphitylation of these amino groups occurred in the previous phosphoramidite methods without base protection. We report that the N-phosphitylation could be considerably suppressed in our new HOBt-mediated coupling strategy via phosphite intermediates as reactive species. Thus, 99.7-99.9% O-selective internucleotidic bond formation was achieved. |
| Keywords: | Chemical synthesis of DNA HOBt O-Selective phosphorylation Activator Phosphoramidite approach without base protection |
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