Efficient desymmetrization of 4,6-di-O-benzyl-myo-inositol by Lipozyme TL-IM

• TL-IM lipase as an eficient catalyst for fast desymmetrization of 4,6-di-O-benzyl-myo-inositol.
• TL-IM lipase acylates 4,6-di-O-benzyl-myo-inositol to 1D-1-O-acetyl-4,6-di-O-benzyl-myo-inositol.
• Good desymmetrization performance in vinyl acetate/hexane mixture.
• Increase of temperature allowed the use of lower loads of biocatalyst.
• The lipase in vinyl acetate/hexane at 30 °C was reused three times.

The enantioselective enzymatic desymmetrization of 4,6-di-O-benzyl-myo-inositol, a myo-inositol derivative, was effectively catalyzed by Thermomyces lanuginosus lipase (TL-IM). The product 1D-1-O-acetyl-4,6-di-O-benzyl-myo-inositol, a useful precursor to inositol phosphates, was obtained in excellent yield and enantiomeric excess. Through the investigation of the effects of solvent, biocatalyst load, and temperature, a more economical procedure resulted. The feasibility of biocatalyst reuse was also shown.

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