The chlorination of barbituric acid and some of its derivatives by chloroperoxidase |
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| Affiliation: | 1. Division of Medicinal Chemistry, Graduate School of Pharmaceutical Sciences, Duquesne University, Pittsburgh, PA 15282, United States;2. Department of Pharmacology and Toxicology, Indiana University School of Medicine, Indianapolis, IN 46202, United States;3. Hauptman-Woodward Medical Research Institute, 700 Ellicott Street, Buffalo, NY 14203, United States;1. University of Coimbra, CQC, Department of Chemistry, P-3004-535, Coimbra, Portugal;2. Faculty of Sciences and Letters, Department of Physics, Istanbul Kultur University, Atakoy Campus, Bakirkoy, 34156, Istanbul, Turkey;1. Department of Chemistry, Federal University of Lavras, P.O. Box 3037, 37200-000 Lavras, Minas Gerais, Brazil;2. Center for Basic and Applied Research, Faculty of Informatics and Management, University of Hradec Kralove, Rokitanskeho 62, 50003, Czech Republic |
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| Abstract: | Barbituric acid and some of its derivatives are presented as new substrates for the chloroperoxidase from Caldariomyces fumago. These compounds are rapidly converted to the 5-chloro or 5,5-dichloro derivatives, in very high yield. The reaction path is discussed and the kinetics of the reactions are investigated. It is shown that neither the concentration nor the structure of the organic substrate has any influence on the rate of halogenation. The enzymatic chlorination of 1-methyl-5-phenylbarbituric acid does not proceed in a stereoselective manner. The results are compared with the present theories concerning the enzymatic reaction mechanism, and the current research on this topic is evaluated. The available data do not as yet permit a definitive choice of reaction mechanism. |
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