title: Transformation of thiols to disulfides by epolactaene and its derivatives.
abstract: 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.
authors.affiliation: Graduate School of Life and Environmental Sciences, Kyoto Prefectural University, Kyoto 606-8522, Japan. kuramoch@kpu.ac.jp
authors.forename: Kouji
authors.initials: K
authors.lastname: Kuramochi
authors.forename: Takashi
authors.initials: T
authors.lastname: Sunoki
authors.forename: Kazunori
authors.initials: K
authors.lastname: Tsubaki
authors.forename: Yoshiyuki
authors.initials: Y
authors.lastname: Mizushina
authors.forename: Kengo
authors.initials: K
authors.lastname: Sakaguchi
authors.forename: Fumio
authors.initials: F
authors.lastname: Sugawara
authors.forename: Masahiko
authors.initials: M
authors.lastname: Ikekita
authors.forename: Susumu
authors.initials: S
authors.lastname: Kobayashi
mesh_terms: D004220:Disulfides / Q000138:chemical synthesis* / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry; D015394:Molecular Structure; D011090:Polyenes / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D004220:Disulfides; D004852:Epoxy Compounds; D011090:Polyenes; D013438:Sulfhydryl Compounds; C095351:epolactaene