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Synthesis of oligodeoxyribonucleotides containing hydroxymethylphosphonate bonds in the phosphoramidite method and their hybridization properties |
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| Authors: | Akihiro Ohkubo Katsufumi Aoki Yuichi Sato Kohji Seio Mitsuo Sekine |
| Institution: | a Department of Life Science, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 226-8501, Japan b Division of Collaborative Research for Bioscience and Biotechnology, Frontier Collaborative Research Center, Nagatsuta, Midoriku, Yokohama 226-8501, Japan c CREST, JST (Japan Science and Technology Agency), Nagatsuta, Midoriku, Yokohama 226-8501, Japan |
| Abstract: | A set of diastereomeric TpT phosphoramidite building blocks, 1-f and 1-s, containing an alkaline-labile hydroxymethylphosphonate (HMP) linkage were synthesized. Dodecadeoxynucleotides incorporating the HMP bond were also synthesized by use of each stereochemically pure dimer block under mild conditions in the N-unprotected phosphoramidite method. Moreover, it turned out that HMP-oligonucleotides derived from a fast-eluted dimer block exhibit higher affinity for DNA single and double strands than those containing a slow-eluted one. |
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