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Problems of Acyl Migration in Lipase-Catalyzed Enantioselecttve Transformation of Meso-1,3-Diol Systems

1990; Taylor & Francis; Volume: 3; Issue: 1-2 Linguagem: Inglês

10.3109/10242429008992059

0886-4454

Kevin K.-C. Liu, Kenji Nozaki, Chi‐Huey Wong,

Microbial Metabolic Engineering and Bioproduction

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.