Transformation of thiols to disulfides by epolactaene and its derivatives.

Kouji Kuramochi, Takashi Sunoki, Kazunori Tsubaki, Yoshiyuki Mizushina, Kengo Sakaguchi, Fumio Sugawara, Masahiko Ikekita, Susumu Kobayashi

Graduate School of Life and Environmental Sciences, Kyoto Prefectural University, Kyoto 606-8522, Japan. kuramoch@kpu.ac.jp

Bioorganic & medicinal chemistry 2011 Jul 15

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In this paper we report a disulfide formation of thiols induced by epolactaene and its derivatives. We previously reported the disulfide formation of N-acetylcysteine methyl ester by epolactaene in a 1:1 MeOH/0.5M NaHCO(3) aq solution. The present studies reveal that the disulfide formation proceeds under mild conditions such as in PBS at pH 7.3, suggesting that epolactaene may induce disulfide formation of cellular thiols. This compound induces the disulfide formation of several thiols in a 1:1 MeOH/0.5M NaHCO(3) aq solution at room temperature. Moreover, our results show that the acyl side-chain of epolactaene greatly influences the products of the reaction. We analyzed the reaction mechanism by using thiolysis products of epolactaene derivatives and propose a new reaction mechanism. Copyright © 2011 Elsevier Ltd. All rights reserved.

Citation

Kouji Kuramochi, Takashi Sunoki, Kazunori Tsubaki, Yoshiyuki Mizushina, Kengo Sakaguchi, Fumio Sugawara, Masahiko Ikekita, Susumu Kobayashi. Transformation of thiols to disulfides by epolactaene and its derivatives. Bioorganic & medicinal chemistry. 2011 Jul 15;19(14):4162-72