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Keywords:

  • biocatalysis;
  • catalytic promiscuity;
  • Michael addition;
  • nitroaldehydes;
  • tautomerases
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Exploiting catalytic promiscuity: The proline-based enzyme 4-oxalocrotonate tautomerase (4-OT) promiscuously catalyzes asymmetric Michael-type additions of linear aldehydes—ranging from acetaldehyde to octanal—to trans-β-nitrostyrene in aqueous solvent. The presence of 1.4 mol % of 4-OT effected formation of the anticipated γ-nitroaldehydes in fair to good yields with dr values of up to 93:7 and ee values of up to 81 %.