Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 19, Issue 14, Pages 4162-4172Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2011.06.015
Keywords
Epolactaene; gamma-Lactam; Epoxide; Thiol; Disulfide; Thiolysis
Funding
- Grants-in-Aid for Scientific Research [22390004] Funding Source: KAKEN
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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/0.5 M 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/0.5 M 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. (C) 2011 Elsevier Ltd. All rights reserved.
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