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Phenoxazinone synthesis by human hemoglobin.

A Tomoda¹, H Hamashima, M Arisawa

¹Department of Biochemistry, Tokyo Medical College, Japan.

Biochimica Et Biophysica Acta

|October 27, 1992

Summary

Human hemoglobin catalyzes the conversion of 2-amino-5-methylphenol into a reddish-brown compound, identified as a specific phenoxazinone. This reaction is linked to hemoglobin

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Area of Science:

Biochemistry
Chemical Biology

Background:

Human hemoglobin is a critical protein involved in oxygen transport.
The interaction between small molecules and hemoglobin can lead to biochemical transformations.

Purpose of the Study:

To investigate the reaction between 2-amino-5-methylphenol and human hemoglobin.
To identify the product formed and elucidate the reaction mechanism.

Main Methods:

Spectroscopic analysis including NMR, IR, EI mass spectrometry, and absorption spectra.
Kinetic studies of phenoxazinone production and hemoglobin redox state changes.
Experiments conducted under aerobic and anaerobic conditions with purified hemoglobin and erythrocytes.

Main Results:

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2-amino-5-methylphenol is converted to 2-amino-4,4 alpha-dihydro-4 alpha,7-dimethyl-3H-phenoxazin-3-one.

The reaction is catalyzed by purified hemoglobin, erythrocyte lysates, and intact erythrocytes.

Phenoxazinone production is coupled with the oxidation of ferrous hemoglobin and reduction of ferric hemoglobin under aerobic conditions.

Conclusions:

The reaction mechanism involves the redox cycling of hemoglobin.
The study proposes a detailed mechanism for the transformation of 2-amino-5-methylphenol mediated by hemoglobin.