title: Combination of Novozym 435-catalyzed enantioselective hydrolysis and amidation for the preparation of optically active δ-hexadecalactone.
abstract: A new enzymatic method for synthesis of enantiomerically enriched δ-hexadecalactone (3) based on the enzymatic kinetic resolution of N-methyl-5-acetoxyhexadecanamide (1) is described. A combination of lipase-catalyzed hydrolysis and amidation improved enantioselectivity. Lipase-catalyzed amidation was also investigated. Detailed screening of solvents and additive amines was performed. The addition of cyclohexylamine to lipase-catalyzed hydrolysis afforded the best results to give both enantiomers of 3 with more than 90% enantiomeric excess.
authors.affiliation: Department of Biotechnology and Environmental Chemistry, Kitami Institute of Technology.
authors.forename: Yasutaka
authors.initials: Y
authors.lastname: Shimotori
authors.forename: Masayuki
authors.initials: M
authors.lastname: Hoshi
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Miyakoshi
mesh_terms: D000577:Amides / Q000737:chemistry*; D000588:Amines; D002384:Catalysis; D003514:Cyclohexylamines / Q000737:chemistry; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D006868:Hydrolysis; D007783:Lactones / Q000138:chemical synthesis*; D008049:Lipase / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis*; D012997:Solvents; D013237:Stereoisomerism
chemical_list: D000577:Amides; D000588:Amines; D003514:Cyclohexylamines; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D007783:Lactones; D011753:Pyrones; D012997:Solvents; C093667:Novozyme 435; D008049:Lipase