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Nucleic Acids Symposium Series 2000 44(1):31-32; doi:10.1093/nass/44.1.31
© 2000 by Oxford University Press
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Chemical synthesis of hydroxymethylphosphbnate {alpha}-DNA

Yuichi Sato, Gohsuke Tateno, Takeshi Wada, Kohji Seio and Mitsuo Sekine

Department of Life Science, Faculty of Bioscience and Biotechnology, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 226, Japan

In this paper, we report the synthesis of hydroxymethylphosphonate {alpha}-DNAs and related compounds by use of the H-phosphonate method. These modified {alpha}-DNAs were designed to improve the inherent poor solubility of well-known methylphosphonate {alpha}-DNAs by introduction of a more hydrophilic hydroxymethylphosphonate function. The hybridization ability of hydroxymethylphosphonate {alpha}-DNAs was studied. We also report a novel strategy for the synthesis of {alpha}-thymidine by use of Cl'-epimerization. The details of the neighboring effect of various 5'- and 3'-hydroxyl protective groups such as carbamoyl groups on the ß->{alpha}conversion will be described.


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