Analysis of Kinetic Resolution Data in Lipase Catalyzed Transesterification between Tributyrylglycerol and 2-Alkanols in Organic Solvents.

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  • HIRATA Hirofumi
    Department of Bioscience and Technology, School of Engineering, Hokkaido Tokai University
  • MAYAMA Motomi
    Department of Bioscience and Technology, School of Engineering, Hokkaido Tokai University
  • KASAHARA Ayumi
    Department of Bioscience and Technology, School of Engineering, Hokkaido Tokai University
  • YANAGISHITA Hiroshi
    National Institute of Materials and Chemical Research
  • SUGIURA Masaaki
    National Institute of Materials and Chemical Research

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  • 有機溶媒中におけるトリブチリルグリセリンと２‐アルカノールとのリパーゼを用いたエステル交換による動力学的分割
  • ユウキ ヨウバイチュウ ニ オケル トリブチリルグリセリン ト 2-アルカノー

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Abstract

Lipase catalyzed transesterification between tributyrylglycerol (1) and 2-alkanols (2) has been studied at 30°C using Pseudomonas cepacia and porcine pancreatic lipases (PCL and PPL), six alcohols, and five kinds of organic solvents. The kinetic resolution data were quantitatively analyzed for resolving the alcohol (ee≥0.95) from the racemate, (RS) - (2). The enantiomeric ratios (E values) of PPL catalysis were larger than those of PCL in all cases. E differed according to solvent and the structure of (2). A reversibility of the transesterification was examined : the equilibrium constants (K) were 0.0150.038 and decreased with increase in the hydrophobicity of solvent. The resolution of (R) - (2) (ee ≥0.95) from (RS) - (2) was thus carried out and the measured optical purity of (R) - (2) was in agreement with that expected from E and K. The resolution of (S) - (2) appeared to be strongly affected by K, i.e., the reverse reaction.

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