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The Oxidative Addition Reaction between Compounds of Resorufin (7-Hydroxy-3H-phenoxazin-3-one) and 2-Mercaptoethanol

✍ Scribed by Trevor M. Kitson

Publisher: Elsevier Science
Year: 1998
Tongue: English
Weight: 227 KB
Volume: 26
Category: Article
ISSN: 0045-2068
DOI: 10.1006/bioo.1998.1079

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✦ Synopsis

2-Mercaptoethanol reacts with the methanesulphonate, the dimethylcarbamate, and the ethyl ether of resorufin (7-hydroxy-3H-phenoxazin-3-one) at 25ЊC and pH 7.4 to give colored products with maximal absorbances at 433, 442, and 481 nm, respectively. NMR spectra of the products show that the hydrogen atom on C-2 has been specifically replaced by the -SCH 2 CH 2 OH group. It is concluded that the thiol adds to the quinonimine ring and that the first-formed product then undergoes spontaneous oxidation to reform the resorufin structure. The implications of these studies toward biochemical work with resorufin derivatives is discussed.

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