Kinetic Resolution and Deracemization of Racemic Amines Using a Reductive Aminase

Authors :: Godwin A. Aleku
Juan Mangas-Sanchez
Joan Citoler
Scott P. France
Sarah L. Montgomery
Rachel S. Heath
Matthew P. Thompson
Nicholas J. Turner
Source :: Aleku, G A, Mangas-Sanchez, J, Citoler, J, France, S P, Montgomery, S L, Heath, R S, Thompson, M P & Turner, N J 2018, ' Kinetic Resolution and Deracemization of Racemic Amines Using a Reductive Aminase ', ChemCatChem, vol. 10, no. 3, pp. 515-519 . https://doi.org/10.1002/cctc.201701484, ChemCatChem
Publication Year :: 2018
Publisher :: Wiley, 2018.
Abstract: The NADP(H)-dependent reductive aminase from Aspergillus oryzae (AspRedAm) was combined with an NADPH oxidase (NOX) to develop a redox system that recycles the co-factor. The AspRedAm-NOX system was applied initially for the kinetic resolution of a variety of racemic secondary and primary amines to yield S-configured amines with enantiomeric excess (ee) values up to 99 %. The addition of ammonia borane to this system enabled the efficient deracemization of racemic amines, including the pharmaceutical drug rasagiline and the natural product salsolidine, with conversions up to >98 % and >99 % ee Furthermore, by using the AspRedAm W210A variant it was possible to generate the opposite R enantiomers with efficiency comparable to, or even better than, the wildtype AspRedAm.

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