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  • Title: Efficient preparation of (R)-3-hydroxypentanenitrile with high enantiomeric excess by enzymatic reduction with subsequent enhancement of the optical purity by lipase-catalyzed ester hydrolysis.
    Author: Kawano S, Hasegawa J, Yasohara Y.
    Journal: Biosci Biotechnol Biochem; 2012; 76(9):1796-8. PubMed ID: 22972335.
    Abstract:
    An efficient chemo-enzymatic procedure for the synthesis of (R)-3-hydroxypentanenitrile (1) with over 99% enantiomeric excess using two enzymatic reactions was successfully established. Initial enantioselective enzymatic reduction of 3-oxopentanenitrile with reductase S1 gave (R)-1 with an 81.5% ee which was then converted to (R)-1-(cyanomethyl) propyl n-butyrate (3b). Subsequent lipase-catalyzed enantioselective hydrolysis of 3b gave (R)-1 in a high yield with over 99% ee.
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