Conversion of alcohols to enantiopure amines through dual-enzyme hydrogen-borrowing cascades

• Autores: Francesco G. Mutti, Tanja Knaus, Nigel S. Scrutton
• Localización: Science, ISSN 0036-8075, Vol. 349, Nº 6255, 2015, págs. 1525-1529
• Idioma: inglés
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• Resumen

  • α-Chiral amines are key intermediates for the synthesis of a plethora of chemical compounds at industrial scale. We present a biocatalytic hydrogen-borrowing amination of primary and secondary alcohols that allows for the efficient and environmentally benign production of enantiopure amines. The method relies on a combination of two enzymes: an alcohol dehydrogenase (from Aromatoleum sp., Lactobacillus sp., or Bacillus sp.) operating in tandem with an amine dehydrogenase (engineered from Bacillus sp.) to aminate a structurally diverse range of aromatic and aliphatic alcohols, yielding up to 96% conversion and 99% enantiomeric excess. Primary alcohols were aminated with high conversion (up to 99%). This redox self-sufficient cascade possesses high atom efficiency, sourcing nitrogen from ammonium and generating water as the sole by-product.