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Nucleic Acids Symposium Series 2000 44(1):25-26; doi:10.1093/nass/44.1.25
© 2000 by Oxford University Press
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Study on highly diastereoselective synthesis of (2'R)-2'-deoxy[2'-2H]guanosine

Etsuko Kawashima1, Yu-suke Terui1, Yoshiharu Ishido1 and Kenzo Yokozeki2

1 School of Pharmacy, Tokyo University of Pharmacy and Life Science, 2 AminoScience Laboratories of Ajinomoto Co., Inc.

To develop an efficient method for the synthesis of a highly diastereoselective (2'R)-2'-deoxy[2'-2H]guanoslne (1), studies of organic chemical conversion from 2'-bromo-2'-deoxy-N2-isobutyryl-3',5'-O-TIPDS-guanosine (2) to 1 and a biological transdeoxyribofuranosylation of (2'R>98 % de)-2'-deoxy[2'-2H]uridine (4) were carried out. As the results, a highly diastereoselective synthesis of 1 was achieved by a biological transdeoxyribo-furanosylation between 2,6-diaminopurine and 4 by the use of Enterobacter aerogenes AJ-11125, followed by treatment with adenosine deaminase. The results will be described in detail.


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