Problems of Acyl Migration in Lipase-Catalyzed Enantioselecttve Transformation of Meso-1,3-Diol Systems |
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| Authors: | Kevin K -C Liu Kenji Nozaki Chi-Huey Wong |
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| Institution: |
a Department of Chemistry, Texas A&M University, College Station, Texas
b Chemical Synthesis Research Laboratory, Taiho Pharmaceutical Co., Ltd., Kodama-gun, Saitama, Japan
c Department of Chemistry, The Research Institute of Scripps Clinic, La Jolla, CA |
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| Abstract: | In the enantioselective hydrolysis of the di-O-acetyl derivatives of meso-1,3-diol catalyzed by lipases, racemization of the monoacetate products occurs due to non-enzymatic general base-catalyzed acyl migration. The rate of acyl migration increases with increase of pH and buffer concentration. A mechanism of the migration has been proposed to proceed through a six-member ring transition that accounts for the experimental results. The acyl migration, however, was not observed in the enantioselective transesterification of meso-1,3-diols in neutral organic solvents. |
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| Keywords: | Lipase catalysis acyl migration hydrolysis transesterification |
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