14. Enzymatic Stereoselective Synthesis of β-Amino Acids
- Sergio Riva3 and
- Wolf-Dieter Fessner4
Published Online: 27 JUN 2014
Copyright © 2014 Wiley-VCH Verlag GmbH & Co. KGaA
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
Istituto di Chimica del, Riconoscimento Molecolare, C. N. R., Via Mario Bianco 9, 20131 Milano, Italy
Technische Universität, Darmstadt, Department of Organic, Chemistry and Biochemistry, Petersenstr. 22, D-64287 Darmstadt, Germany
- Published Online: 27 JUN 2014
- Published Print: 23 JUL 2014
Print ISBN: 9783527335220
Online ISBN: 9783527682492
- β-amino acid;
- nitrile hydratase;
- kinetic resolution;
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.