14. Enzymatic Stereoselective Synthesis of β-Amino Acids

  1. Sergio Riva3 and
  2. Wolf-Dieter Fessner4
  1. Varsha Chhiba1,
  2. Moira Bode2,
  3. Kgama Mathiba1 and
  4. Dean Brady1,2

Published Online: 27 JUN 2014

DOI: 10.1002/9783527682492.ch14

Cascade Biocatalysis : Integrating Stereoselective and Environmentally Friendly Reactions

Cascade Biocatalysis : Integrating Stereoselective and Environmentally Friendly Reactions

How to Cite

Chhiba, V., Bode, M., Mathiba, K. and Brady, D. (2014) Enzymatic Stereoselective Synthesis of β-Amino Acids, 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.ch14

Editor Information

  1. 3

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

  2. 4

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

Author Information

  1. 1

    CSIR Biosciences, Scientia campus, CSIR, Meiring Naude Road, 395, Pretoria, 0184, South Africa

  2. 2

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

Publication History

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

ISBN Information

Print ISBN: 9783527335220

Online ISBN: 9783527682492

SEARCH

Keywords:

  • β-amino acid;
  • peptidomimetics;
  • nitrilase;
  • nitrile hydratase;
  • kinetic resolution;
  • amidase

Summary

The use of enzymes for the enantioselective synthesis of single enantiomer β-subsituted compounds is of interest, as this structural motif occurs commonly in compounds of pharmaceutical importance, such as adrenergic agents, antidiabetics, antimicrobials, and as nonstandard amino acids in therapeutic peptides or peptidomimetics. Access to these compounds can be achieved through diverse synthetic routes with enantioselective steps catalyzed in different ways, including by means of nitrile hydrolysis.

The selectivity of nitrile biocatalysts has been demonstrated on various nitrile-containing substrates. Enantioselectivity has been achieved using either nitrilases or nitrile hydratase-amidase pairs in a cascade reaction. Nitrile-hydrolysing Rhodococci have been applied in the synthesis of both β3-amino and β2-amino acids.

These discoveries are broadening the biocatalytic toolbox available for the sysnthesis of single enantiomer β-subsituted amino acids and amides.