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

Seiji Shinkai; Shinji Yamada; Reiko Ando; Toyoki Kunitake

doi:10.1016/0045-2068(80)90024-3

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

Seiji Shinkai, Shinji Yamada, Reiko Ando, Toyoki Kunitake

Institute for Advanced Study

Research output: Contribution to journal › Article

4 Citations (Scopus)

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 language	English
Pages (from-to)	238-247
Number of pages	10
Journal	Bioorganic Chemistry
Volume	9
Issue number	2
DOIs	https://doi.org/10.1016/0045-2068(80)90024-3
Publication status	Published - Jan 1 1980

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All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Biology
Drug Discovery
Organic Chemistry

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Shinkai, S., Yamada, S., Ando, R., & Kunitake, T. (1980). A flavoenzyme model: Facile oxidation of thiols by a flavin immobilized in cationic polyelectrolytes. Bioorganic Chemistry, 9(2), 238-247. https://doi.org/10.1016/0045-2068(80)90024-3

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AB - 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.

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10.1016/0045-2068(80)90024-3