BioChem - DOS

Asymmetric Reductive Amination of Ketones Catalyzed by Imine Reductases

ChemCatChem

Wetzl, Dennis; Gand, Martin; Ross, Alfred; Mü ller, Hubertus; Matzel, Philipp; Hanlon, Steven P.; Mü ller, Michael; Wirz, Beat; Hö hne, Matthias; Iding, Hans

<P><B>Abstract</B></P><P>Biocatalysis employing imine reductases is a promising approach for the one&#8208;step generation of chiral amines from ketones. The enzymes reported for this process suffer from low activity and moderate stereoselectivity. We identified a set of enzymes that facilitate this reaction with high to quantitative conversions from a library of 28 imine reductases. This enabled the conversion of ketones with ammonia, methylamine, or butylamine into the corresponding amines. Most importantly, we performed preparative (>100 mg) scale syntheses of amines such as (1<I>S</I>,3<I>R</I>)&#8208;<I>N</I>,3&#8208;dimethylcyclohexylamine and (<I>R</I>)&#8208;<I>N</I>&#8208;methyl&#8208;2&#8208;aminohexane with excellent stereochemical purities (98 % <I>de</I>, 96 % <I>ee</I>) in good yields.</P>

2016

1867-3880

1867-3899

8

12

pp.2023-2026

10.1002/cctc.201600384

http://click.ndsl.kr/servlet/OpenAPIDetailView?keyValue=05787966&target=NART&cn=NART79039057

amines; asymmetric synthesis; biocatalysis; imine reductase; reductive amination