Lactones 12. Enzymatic lactonization of gamma,delta-epoxy esters by the apple fruit and Jerusalem artichoke bulb |
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Authors: | Olejniczak Teresa Mironowicz Agnieszka Wawrzeńczyk Czesław |
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Institution: | Department of Chemistry, Agricultural University, Norwida 25, 50-375 Wroc?aw, Poland. |
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Abstract: | The enzymatic lactonization of three acyclic gamma, delta-epoxy esters (ethyl 3,7-dimethyl-4,5-epoxyoctanoate, ethyl 3,7,7-trimethyl-4,5-epoxyoctanoate, and ethyl 3,3,7-trimethyl-4,5-epoxyoctanoate) by apple fruit (Malus silvestris) and Jerusalem artichoke bulb (Helianthus tuberosus L.) was investigated. The substrates were transformed into a mixture of isomeric delta-hydroxy-gamma-lactones and gamma-hydroxy-delta-lactones. The gamma-lactones (yields ranging from 45-70%) predominated over delta-lactones (yields ranging from 8-40%). The composition of the product mixture depended on the structure of substrate as well as the biocatalyst. The enzymatic system in these biocatalysts also exhibited diastereoselectivity and enantioselectivity. |
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Keywords: | Malus silvestris Helianthus tuberosus Biotransformations Lactonization γ δ-Epoxy esters δ-Hydroxy-γ-lactones γ-Hydroxy-δ-lactones |
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