Lactones 12.: Enzymatic lactonization of γ,δ-epoxy esters by the apple fruit and Jerusalem artichoke bulb
✍ Scribed by Teresa Olejniczak; Agnieszka Mironowicz; Czesław Wawrzeńczyk
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- English
- Weight
- 124 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0045-2068
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✦ Synopsis
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.