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

ABSTRACT: ?-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.

SUBMITTER: Mutti FG

PROVIDER: S-EPMC4883652 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

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

Mutti Francesco G FG Knaus Tanja T Scrutton Nigel S NS Breuer Michael M Turner Nicholas J NJ

Science (New York, N.Y.) 20150901 6255

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 Bacillu ...[more]

PMID: 26404833

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