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Paper | Regular issue | Vol 45, No. 1, 1997, pp.157-162
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7656
Substituent Effect of an N-Amino Group on the H-D Exchange of Ring Hydrogens of Adenines Compared with an N-Methyl Group

Wei Wu, Tetsuya Saga, Isamu Terashima, Ken-ichi Saeki, Kohfuku Kohda,* and Yutaka Kawazoe

*Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan

Abstract

Substituent effects of an N-amino group on the H-D exchange of ring hydrogens of adenines were compared with those of N-methyl group by treating N3-, N7-, and N9-substituted adenines in phosphate buffered D2O media at 70 °C. N-Aminoadenines underwent H-D exchange in position 8 faster than the corresponding N-methyladenines. Rates of the exchange of C8-hydrogen of N9-substituted adenines were independent of pD of the medium in an ordinary pD range above their pKa. In strongly alkaline media, N9-aminoadenine underwent H-D exchange at position 2, but N9-methyladenine did not.