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The Strathprints institutional repository is a digital archive of University of Strathclyde's Open Access research outputs. Strathprints provides access to thousands of Open Access research papers by University of Strathclyde researchers, including by researchers from the Department of Computer & Information Sciences involved in mathematically structured programming, similarity and metric search, computer security, software systems, combinatronics and digital health.

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A novel biotransformation of benzofurans and related compounds catalysed by a chloroperoxidase

Alvarez, Ricardo G. and Hunter, Iain S. and Suckling, Colin J. and Thomas, Michael and Vitinius, Ute (2001) A novel biotransformation of benzofurans and related compounds catalysed by a chloroperoxidase. Tetrahedron, 57 (40). pp. 8581-8587. ISSN 0040-4020

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Abstract

Abstract The oxidation of 3-alkyl benzofurans, indoles, and a benzothiophene by the chloroperoxidase from Caldariomyces fumago has been investigated. Under conditions in which the catalase activity of chloroperoxidase was minimised in the presence of chloride and hydrogen peroxide, 3-methylbenzothiophene was oxidised at sulfur but the indoles (5-9) and benzofurans (1-4) gave 2,3-diols as initial products. In the case of N-unsubstituted indoles, these tautomerised to give the corresponding lactam. In contrast, the diols (predominantly trans) formed from the benzofurans were sufficiently stable for isolation and full characterisation. This novel reaction has the potential to be developed into a useful synthetic biotransformation.