title: Enzymatically enantioselective hydrolysis of prochiral 1,3-diacyloxyglycerol derivatives.
abstract: An enzymatically enantioselective ester hydrolysis of prochiral 1,3-diacyloxy-2-substituted-2-propanol to chiral 1-acyloxy-2,3-propanediol was studied. The (R)-monoester was prepared by selection of a suitable lipase and alkyl chain length of the substrate diester. Lipase D from Rhizopus delemer gave (R)-1-isobutyryloxy-2-(2,4-difluorophenyl)-2,3-propanediol with 97%ee and 87% yield at 15 degrees C and pH 5.5. The (R)-monoester is a key intermediate of azole antifungal agents.
authors.affiliation: Fine Chemicals Research Laboratories, Kaneka Corporation, Takasago, Hyogo, Japan. Yoshihiko.Yasohara@kaneka.co.jp
authors.forename: Y
authors.initials: Y
authors.lastname: Yasohara
authors.forename: N
authors.initials: N
authors.lastname: Kizaki
authors.forename: K
authors.initials: K
authors.lastname: Miyamoto
authors.forename: J
authors.initials: J
authors.lastname: Hasegawa
authors.forename: T
authors.initials: T
authors.lastname: Ohashi
mesh_terms: D001671:Biochemistry / Q000379:methods*; D004075:Diglycerides / Q000737:chemistry*; D005464:Fluorobenzenes / Q000737:chemistry; D005989:Glycerides / Q000737:chemistry; D006868:Hydrolysis; D008049:Lipase / Q000737:chemistry / Q000378:metabolism*; D012233:Rhizopus / Q000201:enzymology; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: C453470:1-isobutyryloxy-2-(2,4-difluorophenyl)-2,3-propanediol; D004075:Diglycerides; D005464:Fluorobenzenes; D005989:Glycerides; D012997:Solvents; D008049:Lipase