Intermediate and mechanism of hydroxylation of o-iodophenol by salicylate hydroxylase.

Intermediate and mechanism of hydroxylation of o-iodophenol by salicylate hydroxylase. Research Abstract Details 

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Intermediate and mechanism of hydroxylation of o-iodophenol by salicylate hydroxylase. Abstract Text:

K Suzuki,T Gomi,E Itagaki,

Salicylate hydroxylase [EC 1.14.13.1] from Pseudomonas putida catalyzes the hydroxylation of salicylate, and also o-aminophenol, o-nitrophenol, and o-halogenophenols, to catechol. The reactions with these o-substituted phenols comprise oxygenative deamination, denitration, and dehalogenation, respectively. The reaction stoichiometry, as to NADH oxidized, oxygen consumed, and catechol formed, is 2 : 1 : 1, respectively. The mechanisms for the deiodination and oxygenation of o-iodophenol were investigated in detail by the use of I(+)-trapping reagents such as DL-methionine, 2-chlorodimedone, and L-tyrosine. The addition of the traps did not change the molar ratio of catechol formed to NADH oxidized, nor iodinated traps produced were in the incubation mixture. The results suggest that I+ was not produced on the deiodination in the hydroxylation of o-iodophenol. On the other hand, L-ascorbate, L-epinephrine, and phenylhydrazine increased the molar ratio. o-Phenylenediamine decreased it, being converted to phenazine. This suggests that o-benzoquinone is formed in the oxidation of o-iodophenol as a nascent product. The quinone was detected spectrophotometrically by means of the stopped-flow method. Kinetic analysis of the reactions revealed that o-benzoquinone is reduced nonenzymatically to catechol by a second molecule of NADH. A mechanism of elimination for the ortho-substituted groups of substrate phenols by the enzyme is proposed and discussed.

Intermediate and mechanism of hydroxylation of o-iodophenol by salicylate hydroxylase. Publishing Authors By Initials

K Suzuki,T Gomi,E Itagaki,

For similar bacteria: gram-negative bacteria: gram-negative aerobic bacteria: gram-negative aerobic rods and cocci: pseudomonadaceae: pseudomonas research abstracts see: bacteria: gram-negative bacteria: gram-negative aerobic bacteria: gram-negative aerobic rods and cocci: pseudomonadaceae: pseudomonas research

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Intermediate and mechanism of hydroxylation of o-iodophenol by salicylate hydroxylase. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Journal of biochemistry

VOLUME: 109

Page Numbers: 791-7

Journal Abbreviation: J. Biochem.

ISSN: 0021-924X

DAY: 19

MONTH: May

YEAR: 1991

Intermediate and mechanism of hydroxylation of o-iodophenol by salicylate hydroxylase. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 376600

Intermediate and mechanism of hydroxylation of o-iodophenol by salicylate hydroxylase. Keywords Mesh Terms:

KEYWORDS: Pseudomonas

MESH TERMS: enzymology

Chemical & Substance for Abstract: Intermediate and mechanism of hydroxylation of o-iodophenol by salicylate hydroxylase. Information

Substance Name: salicylate 1-monooxygenase

Registry Number: EC 1.14.13.1

Grant and Affiliation Information for Intermediate and mechanism of hydroxylation of o-iodophenol by salicylate hydroxylase.

AFFILIATION: Department of Chemistry, Faculty of Science, Kanazawa University, Ishikawa.

Country: JAPAN

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MEDLINETA: J Biochem

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