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Chiral Amine Synthesis Using ω‐Transaminases: An Amine Donor that Displaces Equilibria and Enables High‐Throughput Screening

2014; Wiley; Volume: 53; Issue: 40 Linguagem: Inglês

10.1002/anie.201406571

1521-3773

Anthony P. Green, Nicholas J. Turner, Elaine O’Reilly,

Carbohydrate Chemistry and Synthesis

Abstract The widespread application of ω‐transaminases as biocatalysts for chiral amine synthesis has been hampered by fundamental challenges, including unfavorable equilibrium positions and product inhibition. Herein, an efficient process that allows reactions to proceed in high conversion in the absence of by‐product removal using only one equivalent of a diamine donor ( ortho ‐xylylenediamine) is reported. This operationally simple method is compatible with the most widely used ( R )‐ and ( S )‐selective ω‐TAs and is particularly suitable for the conversion of substrates with unfavorable equilibrium positions (e.g., 1‐indanone). Significantly, spontaneous polymerization of the isoindole by‐product generates colored derivatives, providing a high‐throughput screening platform to identify desired ω‐TA activity.