Enzymatically enantioselective hydrolysis of prochiral 1,3-diacyloxyglycerol derivatives.
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.
Yasohara
Y
Y
Fine Chemicals Research Laboratories, Kaneka Corporation, Takasago, Hyogo, Japan. Yoshihiko.Yasohara@kaneka.co.jp
Kizaki
N
N
Miyamoto
K
K
Hasegawa
J
J
Ohashi
T
T
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
C453470:1-isobutyryloxy-2-(2,4-difluorophenyl)-2,3-propanediol; D004075:Diglycerides; D005464:Fluorobenzenes; D005989:Glycerides; D012997:Solvents; D008049:Lipase