Enantioselective reduction of sulfur-containing cyclic imines through biocatalysis

Nadine Zumbrägel, Christian Merten, Stefan M. Huber and Harald Gröger ()
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Nadine Zumbrägel: Bielefeld University
Christian Merten: Ruhr-University Bochum
Stefan M. Huber: Ruhr-University Bochum
Harald Gröger: Bielefeld University

Nature Communications, 2018, vol. 9, issue 1, 1-9

Abstract: Abstract The 3-thiazolidine ring represents an important structural motif in life sciences molecules. However, up to now reduction of 3-thiazolines as an attractive approach failed by means of nearly all chemical reduction technologies for imines. Thus, the development of an efficient general and enantioselective synthetic technology giving access to a range of such heterocycles remained a challenge. Here we present a method enabling the reduction of 3-thiazolines with high conversion and high to excellent enantioselectivity (at least 96% and up to 99% enantiomeric excess). This technology is based on the use of imine reductases as catalysts, has a broad substrate range, and is also applied successfully to other sulfur-containing heterocyclic imines such as 2H-1,4-benzothiazines. Moreover the effiency of this biocatalytic technology platform is demonstrated in an initial process development leading to 99% conversion and 99% enantiomeric excess at a substrate loading of 18 g/L in the presence of designer cells.

Date: 2018
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DOI: 10.1038/s41467-018-03841-5

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