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  • Title: Asymmetric synthesis of both antipodes of beta-hydroxy nitriles and beta-hydroxy carboxylic acids via enzymatic reduction or sequential reduction/hydrolysis.
    Author: Ankati H, Zhu D, Yang Y, Biehl ER, Hua L.
    Journal: J Org Chem; 2009 Feb 20; 74(4):1658-62. PubMed ID: 19161324.
    Abstract:
    Use of isolated carbonyl reductases in the reduction of aromatic beta-ketonitriles have completely eliminated the competing alpha-ethylation, which is often observed with whole cell biocatalysts. By choosing suitable recombinant carbonyl reductase, the reduction of beta-ketonitriles afforded (R)- or (S)-beta-hydroxy nitriles with excellent optical purity and yield. Subsequently, nitrilase-catalyzed hydrolysis of the obtained optically pure beta-hydroxy nitriles led to the corresponding beta-hydroxy carboxylic acids in high yields. More importantly, the sequential enzymatic reduction and hydrolysis could be carried out in "two-step-one-pot" fashion without the isolation of intermediates beta-hydroxy nitriles, lowering the cost and minimizing the environmental impact. This allows ready access to both antipodes of chiral beta-hydroxy nitriles and beta-hydroxy carboxylic acids of pharmaceutical importance with excellent optical purity.
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