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.
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.
authors.affiliation: Frontier Biochemical and Medical Research Laboratories, Kaneka Corporation, 1-8 Miyame, Takasago, Hyogo 676-8688, Japan. Shigeru_Kawano@kn.kaneka.co.jp
authors.forename: Shigeru
authors.initials: S
authors.lastname: Kawano
authors.forename: Junzo
authors.initials: J
authors.lastname: Hasegawa
authors.forename: Yoshihiko
authors.initials: Y
authors.lastname: Yasohara
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis*; D002087:Butyrates / Q000737:chemistry; D002384:Catalysis; D004952:Esters; D006868:Hydrolysis; D008049:Lipase / Q000737:chemistry*; D009570:Nitriles / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D000439:Pentanols / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D002087:Butyrates; D004952:Esters; D009570:Nitriles; D000439:Pentanols; D008049:Lipase