Imine Reductases, Reductive Aminases, and Amine Oxidases for the Synthesis of Chiral Amines: Discovery, Characterization, and Synthetic Applications

Cosgrove, Sebastian C.; Brzezniak, Agata; France, Scott P.; Ramsden, Jeremy I.; Mangas-Sanchez, Juan; Montgomery, Sarah L.; Heath, Rachel S.; Turner, Nicholas J.

Abstract

Synthesis of the chiral amine moiety is a key challenge for synthetic organic chemistry due to its prevalence in many biologically active molecules. Imine reductase and amine oxidase enzymes have enabled the biocatalytic synthesis of a host of chiral amine compounds. In this chapter, procedures for the synthesis of chiral amines using imine reductases (IREDs), the recently discovered IRED homologues reductive aminases, and amine oxidases (AOs) are described. Amine oxidases have been the subject of mutagenesis approaches for improvement of substrate scope. The high-throughput screening method for determining active variants in amine oxidase libraries is illustrated. Finally, in an approach which takes inspiration from nature, many enzymes can be combined with each other in cascade reactions. The incorporation of imine reductase and monoamine oxidase biocatalysts into several cascade reactions, both in vitro and in vivo (where the approach moves toward synthetic biology), is reported.

Citation

Cosgrove, S. C., Brzezniak, A., France, S. P., Ramsden, J. I., Mangas-Sanchez, J., Montgomery, S. L., …Turner, N. J. (2018). Imine Reductases, Reductive Aminases, and Amine Oxidases for the Synthesis of Chiral Amines: Discovery, Characterization, and Synthetic Applications. In Enzymes in Synthetic Biology (131-149). Elsevier. https://doi.org/10.1016/bs.mie.2018.04.022

• Online Publication Date: May 21, 2018
• Publication Date: Aug 30, 2018
• Deposit Date: Jun 16, 2023
• Publisher: Elsevier
• Pages: 131-149
• Series ISSN: 0076-6879
• Book Title: Enzymes in Synthetic Biology
• Chapter Number: 6
• ISBN: 978-0-12-815148-8
• DOI: https://doi.org/10.1016/bs.mie.2018.04.022