A flavoenzyme model: Facile oxidation of thiols by a flavin immobilized in cationic polyelectrolytes

Seiji Shinkai, Shinji Yamada, Reiko Ando, Toyoki Kunitake

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Abstract

The reactions of a polymer-bound flavin with thiols (2-mercaptoethanol, glutathione, thiophenol, and 1,4-butanedithiol) are remarkably accelerated, when compared with that of a monomeric flavin. The rate enhancements observed were 30- to 6000-fold. In particular, thiophenol which had been believed not to be oxidized by flavin in nonenzymatic systems was oxidized most rapidly among the monothiols examined. The reaction rates were improved by incorporation of a dodecyl group into the flavin-containing polymer. Therefore, the hydrophobic nature of the cationic polymer matrix was concluded to be responsible for the large rate enhancement among other factors.

Original languageEnglish
Pages (from-to)238-247
Number of pages10
JournalBioorganic Chemistry
Volume9
Issue number2
DOIs
Publication statusPublished - Jan 1 1980

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

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