11. Nitrile Converting Enzymes Involved in Natural and Synthetic Cascade Reactions

  1. Sergio Riva7 and
  2. Wolf-Dieter Fessner8
  1. Ludmila Martínková1,
  2. Andreas Stolz2,
  3. Fred van Rantwijk3,
  4. Nicola D'Antona4,
  5. Dean Brady5,6 and
  6. Linda G. Otten3

Published Online: 27 JUN 2014

DOI: 10.1002/9783527682492.ch11

Cascade Biocatalysis : Integrating Stereoselective and Environmentally Friendly Reactions

Cascade Biocatalysis : Integrating Stereoselective and Environmentally Friendly Reactions

How to Cite

Martínková, L., Stolz, A., Rantwijk, F. v., D'Antona, N., Brady, D. and Otten, L. G. (2014) Nitrile Converting Enzymes Involved in Natural and Synthetic Cascade Reactions, in Cascade Biocatalysis : Integrating Stereoselective and Environmentally Friendly Reactions (eds S. Riva and W.-D. Fessner), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany. doi: 10.1002/9783527682492.ch11

Editor Information

  1. 7

    Istituto di Chimica del, Riconoscimento Molecolare, C. N. R., Via Mario Bianco 9, 20131 Milano, Italy

  2. 8

    Technische Universität, Darmstadt, Department of Organic, Chemistry and Biochemistry, Petersenstr. 22, D-64287 Darmstadt, Germany

Author Information

  1. 1

    Academy of Sciences of the Czech Republic, Institute of Microbiology, Laboratory of Biotransformation, Videnská 1083, 142 20, Prague, Czech Republic

  2. 2

    University of Stuttgart, Institute of Microbiology, Allmandring 31, 70569, Stuttgart, Germany

  3. 3

    Delft University of Technology, Department of Biotechnology, Biocatalysis, Julianalaan 136, 2628 BL, Delft, The Netherlands

  4. 4

    CNR National Research Council of Italy, Institute of Biomolecular Chemistry, Via P. Gaifami 18, 95126, Catania, Italy

  5. 5

    University of the Witwatersrand, School of Chemistry, Molecular Sciences Institute, PO Wits, 2050, Johannesburg, South Africa

  6. 6

    CSIR Biosciences, Protein Technologies, Building 18, Meiring Naudé Road, Brummeria, 0001, Pretoria, South Africa

Publication History

  1. Published Online: 27 JUN 2014
  2. Published Print: 23 JUL 2014

ISBN Information

Print ISBN: 9783527335220

Online ISBN: 9783527682492

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Keywords:

  • Nitrile converting enzymes;
  • nitrile hydratase;
  • amidase;
  • nitrilase;
  • aldoxime dehydratase;
  • enantioselectivity;
  • biotransformation;
  • cascade reaction

Summary

Nitrile-containing compounds are abundant in nature, resulting in a plethora of enzymes to metabolize these compounds very efficiently. From a synthetic perspective, nitriles are simple to synthesize through several organic chemical pathways from cheap substrates, which makes them important intermediates in the chemical industry for production of a wide variety of compounds. Nitrile-converting enzymes have been used in many single enzyme and cascade reactions in the past years. The enzymatic part in organic synthesis has usually been performed as a single step, but as nature has attuned whole pathways to metabolize nitriles, multienzymatic cascade reactions are being used more often nowadays

This chapter describes the mechanisms and operation of both natural and artificial cascades developed in the past decade. In addition to describing different enzyme systems, each section shows synthetic applications in academic and industrial settings using these cascades. Most described processes show different enzymatic actions on the same group of a molecule, but enzymatic cascades can also be performed on different regions of the same molecule in order to get to more efficient synthetic pathways.