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

Seiji Shinkai, Thomas C. Bruice

Research output: Contribution to journalArticle

32 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 languageEnglish
Pages (from-to)7526-7528
Number of pages3
JournalJournal of the American Chemical Society
Volume95
Issue number22
DOIs
Publication statusPublished - Oct 1 1973
Externally publishedYes

Fingerprint

Redox reactions
Ketones
Oxidation-Reduction
Methanol
Aldehydes
Alcohols
Oxidation

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Question of Covalent Intermediate Formation in the Flavine-Catalyzed Carbonyl to Carbinol Oxidation-Reduction Reaction. / Shinkai, Seiji; Bruice, Thomas C.

In: Journal of the American Chemical Society, Vol. 95, No. 22, 01.10.1973, p. 7526-7528.

Research output: Contribution to journalArticle

@article{a515ebc2c4624fc8999b7d775a84a886,
title = "Question of Covalent Intermediate Formation in the Flavine-Catalyzed Carbonyl to Carbinol Oxidation-Reduction Reaction",
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",
month = "10",
day = "1",
doi = "10.1021/ja00803a064",
language = "English",
volume = "95",
pages = "7526--7528",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "22",

}

TY - JOUR

T1 - Question of Covalent Intermediate Formation in the Flavine-Catalyzed Carbonyl to Carbinol Oxidation-Reduction Reaction

AU - Shinkai, Seiji

AU - Bruice, Thomas C.

PY - 1973/10/1

Y1 - 1973/10/1

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).

UR - http://www.scopus.com/inward/record.url?scp=0008258981&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0008258981&partnerID=8YFLogxK

U2 - 10.1021/ja00803a064

DO - 10.1021/ja00803a064

M3 - Article

AN - SCOPUS:0008258981

VL - 95

SP - 7526

EP - 7528

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 22

ER -