New Development of Enzyme Utilization in Organic Solvents

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By the catalytic action of a lipase, Saiken 100, primary, secondary, and tertiary alcohols were effectively acylated with trimethylsilylketene in organic media, to give trimethylsilylacetyl esters. The enzyme also successfully acylated a phenol and bulky alcohols as well as a substrate bearing a carboxyl group. The acylation with triethylsilylketene and dimethylphenylsilylketene was also catalyzed by the enzyme.Diketene having a highly strained 4-membered ring and intramolecular enol-ester structure was found to be a powerful acylating agent for lipase mediate acylation of alcohols in organic solvents. The stereoselectivity with a lipase, Amano PS,was extremely high which denied the conventional propose of the catalysis on the protein surface. The remaining alcohols and generated esters were able to be separated easily by simple fractional distilllation. beta-Lactones having the similar structure was also trans-esterified with ring opening stereoselectively which were very important starting materials for natural products synthesis and bio-degradable copolymers.