Photo‐biocatalytic One‐Pot Cascades for the Enantioselective Synthesis of 1,3‐Mercaptoalkanol Volatile Sulfur Compounds

The synthesis of enantiomerically pure 1,3‐mercaptoalkanol volatile sulfur compounds through a one‐pot photo‐biocatalytic cascade reaction is described. Two new KRED biocatalysts with opposite enantioselectivity were discovered and proved to be efficient on a wide range of substrates. The one‐pot ca...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-05, Vol.57 (20), p.5803-5807
Main Authors: Lauder, Kate, Toscani, Anita, Qi, Yuyin, Lim, Jesmine, Charnock, Simon J., Korah, Krupa, Castagnolo, Daniele
Format: Article
Language:English
Subjects:
biocatalysis
Biocatalysts
Cascade chemical reactions
Enantiomers
ketoreductases
mercaptoalkanols
photocatalysis
Substrates
Sulfur
Sulfur compounds
Synthesis
volatile sulfur compounds
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Summary:The synthesis of enantiomerically pure 1,3‐mercaptoalkanol volatile sulfur compounds through a one‐pot photo‐biocatalytic cascade reaction is described. Two new KRED biocatalysts with opposite enantioselectivity were discovered and proved to be efficient on a wide range of substrates. The one‐pot cascade reaction combining photocatalytic thio‐Michael addition with biocatalytic ketoreduction in an aqueous medium provides a green and sustainable approach to enantiomerically pure 1,3‐mercaptoalkanols in high yields with excellent enantioselectivity. A dependable route to volatile products: A one‐pot cascade reaction combining photocatalytic thio‐Michael addition with biocatalytic ketoreduction in an aqueous medium was developed for the synthesis of enantiomerically pure 1,3‐mercaptoalkanols (see scheme). Two new ketoreductase (KRED) biocatalysts with opposite enantioselectivity were discovered and found to reduce a wide range of substrates efficiently.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201802135