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Enantioselective reduction of sulfur-containing cyclic imines through biocatalysis

Author

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  • Nadine Zumbrägel

    (Bielefeld University)

  • Christian Merten

    (Ruhr-University Bochum)

  • Stefan M. Huber

    (Ruhr-University Bochum)

  • Harald Gröger

    (Bielefeld University)

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.

Suggested Citation

  • Nadine Zumbrägel & Christian Merten & Stefan M. Huber & Harald Gröger, 2018. "Enantioselective reduction of sulfur-containing cyclic imines through biocatalysis," Nature Communications, Nature, vol. 9(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-03841-5
    DOI: 10.1038/s41467-018-03841-5
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