Formation of S-[5-(2'-Deoxyuridyl)] thiol Compounds in the Dehalogenation of 5-Bromo- and 5-Iodo-2'-deoxyuridine with Cysteine Derivatives

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概要

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• Dehalogenations of 5-bromo- and 5-iodo-2'-deoxyuridine by thiol compounds in aqueous solutions were studied. The thiols used were cysteine, cysteine methyl- and ethyl-esters, cysteamine, homocysteine, glutathione, 2-mercaptoethanol, and 2-mercaptopropionic acid. The products of these reactions and the rate constants were determined. At pH 8 and 37°, the dehalogenation rates by these thiols decreased in above-mentioned order. 5-Alkylthiouracil derivatives were found in products of the reactions between 5-bromo-2'-deoxyuridine and cysteine, cysteine ethyl ester, cysteamine, homocysteine and glutathione, as well as of the reaction between 5-iodo-2'-deoxyuridine and cysteine. This indicated that the S_N2 mechanism proposed in a previous paper (Y. Wataya, K. Negishi and H. Hayatsu, Biochemistry, 12,3992 (1973)) is generally operating in the dehalogenations of these compounds with thiols.

• 公益社団法人日本薬学会の論文
• 1978-06-25

著者

• 早津 彦哉

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 早津 彦哉

  Faculty Of Pharmaceutical Sciences Okayama University

• 早津 彦哉

  岡山大 薬 遺伝子実験施設

• 根岸 和雄

  Faculty of Pharmaceutical Sciences, Okayama University

• 知久馬 敏幸

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 根岸 和雄

  Okayama University Advanced Science Research Center:nihon Pharmaceutical University

• 知久馬 敏幸

  Faculty Of Pharmaceutical Sciences University Of Tokyo:(present Address)showa College Of Pharmacy:(p

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