Question of Covalent Intermediate Formation in the Flavine-Catalyzed Carbonyl to Carbinol Oxidation-Reduction Reaction

Seiji Shinkai; Thomas C. Bruice

doi:10.1021/ja00803a064

Question of Covalent Intermediate Formation in the Flavine-Catalyzed Carbonyl to Carbinol Oxidation-Reduction Reaction

Seiji Shinkai, Thomas C. Bruice

Research output: Contribution to journal › Article › peer-review

33 Citations (Scopus)

Abstract

The mechanisms by which flavoenzymes catalyze oxidation-reduction reactions are of much concern. We address ourselves herein to the interconversion of aldehydes (ketones) and alcohols coupled to the oxidation-reduction of flavine. In a study of the oxidation of 10-phenylisoalloxazine Brown and Hamilton¹ proposed 4a addition of alkoxide followed by base-catalyzed elimination of ketone (eq 1).

Original language	English
Pages (from-to)	7526-7528
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	95
Issue number	22
DOIs	https://doi.org/10.1021/ja00803a064
Publication status	Published - Oct 1 1973
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja00803a064

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abstract = "The mechanisms by which flavoenzymes catalyze oxidation-reduction reactions are of much concern. We address ourselves herein to the interconversion of aldehydes (ketones) and alcohols coupled to the oxidation-reduction of flavine. In a study of the oxidation of 10-phenylisoalloxazine Brown and Hamilton1 proposed 4a addition of alkoxide followed by base-catalyzed elimination of ketone (eq 1).",

author = "Seiji Shinkai and Bruice, {Thomas C.}",

year = "1973",

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AU - Bruice, Thomas C.

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N2 - The mechanisms by which flavoenzymes catalyze oxidation-reduction reactions are of much concern. We address ourselves herein to the interconversion of aldehydes (ketones) and alcohols coupled to the oxidation-reduction of flavine. In a study of the oxidation of 10-phenylisoalloxazine Brown and Hamilton1 proposed 4a addition of alkoxide followed by base-catalyzed elimination of ketone (eq 1).

AB - The mechanisms by which flavoenzymes catalyze oxidation-reduction reactions are of much concern. We address ourselves herein to the interconversion of aldehydes (ketones) and alcohols coupled to the oxidation-reduction of flavine. In a study of the oxidation of 10-phenylisoalloxazine Brown and Hamilton1 proposed 4a addition of alkoxide followed by base-catalyzed elimination of ketone (eq 1).

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ER -

Question of Covalent Intermediate Formation in the Flavine-Catalyzed Carbonyl to Carbinol Oxidation-Reduction Reaction

Abstract

All Science Journal Classification (ASJC) codes

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