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Published on: June 13, 2022
Crystallization Assisted Dynamic Kinetic Resolution for the Synthesis of (R)-β-Methylphenethylamine
Feodor Belov1, Alina Gazizova2, Hannah Bork3
1Institute of Chemistry, Biocatalytic Synthesis Group, Otto von Guericke University of Magdeburg, Building 28, Universitätsplatz 2, 39106, Magdeburg, Germany.
Abstract:
This study explores a combination of the concept of enantioselective enzymatic synthesis of β-chiral amines through transamination with in situ product crystallization (ISPC) to overcome product inhibition. Using 2-phenylpropanal as a readily available and easily racemizing substrate of choice, (R)-β-methylphenethylamine ((R)-2-phenylpropan-1-amine) concentrations of up to 250 mM and enantiomeric excesses of up to 99 % are achieved when using a commercially available transaminase from Ruegeria pomeroyi in a fed-batch based dynamic kinetic resolution reaction on preparative scale. The source of substrate decomposition during the reaction is also investigated and the resulting unwanted byproduct formation is successfully reduced to insignificant levels.
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