Enzymatically Enantioselective Hydrolysis of Prochiral 1,3-Diacyloxyglycerol Derivatives |
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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°C and pH 5.5. The (R)-monoester is a key intermediate of azole antifungal agents. |
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Keywords: | enantioselective hydrolysis lipase glycerol derivative |
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