Lactones 29. Enzymatic resolution of racemic γ-lactones |
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Authors: | Małgorzata Fajkowska Robert Obara |
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Institution: | 1. Department of Chemistry, Agricultural University, Norwida 25, 50-375, Wroc?aw, Poland;2. Institute of Chemistry, ?wi?tokrzyska Academy, Ch?cińska 5, 25-020, Kielce, Poland |
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Abstract: | Studies on the application of commercially available enzymes to resolution of the racemic unsaturated γ-lactones: 5-(3-methylbutylidene)-4-methyl-tetrahydrofuran-2-one (1a) and 5-(3,3-dimethylbutylidene)-4-methyl-tetrahydrofuran-2-one (2a) are presented. Lipase PS, Rhizopus niveus lipase, Rhizopus arrhizus lipase, porcine pancreas lipase and hog liver esterase transformed substrates into their respective γ-keto acids with good efficiency (50–75%). Three of them hydrolysed the studied lactones with moderate enantioselectivity. Enantiomeric excesses determined by GC for the unreacted lactones were in the range of 20–60%. Lipase PS preferentially hydrolysed the (+) enantiomers of lactones 1a and 2a whereas R. niveus lipase hydrolysed the (?) enantiomers, respectively. |
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Keywords: | Lactones enzymatic resolution lipase esterase enantioselective hydrolysis |
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