title: Enzymatic synthesis of (-)- and (+)-acetoxyhexamides and (-)- and (+)-hydroxyhexamides.
abstract: The enantioselective hydrolysis of (+/-)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)-benzenesulfona mides 3 with lipase Amano P from Pseudomonas sp. in a water-saturated solvent gave (R)-4-(1-hydroxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide 2 (39%, > 99% ee) and unchanged (S)-3 (50%, 62% ee). On the other hand, enantioselective esterification of (+/-)-2 with lipase Amano P in the presence of vinyl acetate provided (R)-3 (41%, > 99% ee) and unchanged (S)-2 (46%, 78% ee).
authors.affiliation: School of Pharmaceutical Sciences, Toho University, Chiba, Japan.
authors.forename: H
authors.initials: H
authors.lastname: Akita
authors.forename: K
authors.initials: K
authors.lastname: Kurashima
authors.forename: M
authors.initials: M
authors.lastname: Nozawa
authors.forename: T
authors.initials: T
authors.lastname: Kawana
authors.forename: K
authors.initials: K
authors.lastname: Hirayama
authors.forename: K
authors.initials: K
authors.lastname: Seri
authors.forename: Y
authors.initials: Y
authors.lastname: Imamura
mesh_terms: D000092:Acetohexamide / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000107:Acetylation; D001549:Benzamides / Q000138:chemical synthesis* / Q000737:chemistry; D006868:Hydrolysis; D008049:Lipase / Q000737:chemistry*; D011549:Pseudomonas / Q000201:enzymology*; D012997:Solvents; D013237:Stereoisomerism; D014753:Vinyl Compounds; D000096926:Benzenesulfonamides
chemical_list: D000092:Acetohexamide; D001549:Benzamides; D008049:Lipase; D012997:Solvents; D014753:Vinyl Compounds; C020362:hydroxyhexamide; D000096926:Benzenesulfonamides; C011566:vinyl acetate