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Enantioselective Oxidations Catalyzed by Peroxidases and Monooxygenases

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Enzymes in Action

Part of the book series: NATO Science Partnership Sub-Series: 1: ((ASDT,volume 33))

Abstract

Enantiomerically pure sulfoxides are excellent chiral auxiliaries for asymmetric synthesis and in the preparation of several enantiopure biologically active compounds. For these reasons we have explored biocatalytic approaches for the synthesis of sulfoxides based on the use of heme peroxidases and flavin monooxygenases, such as chloroperoxidase (CPO) and cyclohexanone monooxygenase (CMO), respectively. By using isolated enzymes or whole-cell biotransformations, we have prepared alkyl aryl sulfoxides, 1,3-dithioacetal-1-oxides and dialkyl sulfoxides in high enantiomeric excess (ee). Recent experiments from our and other laboratories have shown that chloroperoxidase is also able to catalyze a broad spectrum of stereoselective epoxidation reactions. The substrate repertoire includes substituted styrenes, straight chain aliphatic and cyclic cis-olefins. The enzyme is also able to perform benzylic hydroxylation and hydroxylation of alkynes with high ee.

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Authors and Affiliations

  1. Istituto di Chimica Organica, Facoltà di Farmacia, Università degli Studi di Milano, Via Venezian 21, I 20133, Milano, Italy

    S. Colonna, N. Gaggero & C. Richelmi

  2. Istituto di Biocatalisi e Riconoscimento Molecolare CNR, Via Mario Bianco 9, I 20131, Milano, Italy

    P. Pasta

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  1. S. Colonna
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  3. C. Richelmi
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Editors and Affiliations

  1. Department of Organic Chemistry, NSR Institute for Molecular Structure, Design and Synthesis, University of Nijmegen, The Netherlands

    Binne Zwanenburg

  2. Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Łódź, Poland

    Marian Mikołajczyk  & Piotr Kiełbasiński  & 

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Colonna, S., Gaggero, N., Richelmi, C., Pasta, P. (2000). Enantioselective Oxidations Catalyzed by Peroxidases and Monooxygenases. In: Zwanenburg, B., Mikołajczyk, M., Kiełbasiński, P. (eds) Enzymes in Action. NATO Science Partnership Sub-Series: 1:, vol 33. Springer, Dordrecht. https://doi.org/10.1007/978-94-010-0924-9_7

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  • DOI: https://doi.org/10.1007/978-94-010-0924-9_7

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-0-7923-6696-6

  • Online ISBN: 978-94-010-0924-9

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