title: Lactones 12. Enzymatic lactonization of gamma, delta-epoxy esters by the apple fruit and Jerusalem artichoke bulb.
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.
authors.affiliation: Department of Chemistry, Agricultural University, Norwida 25, 50-375 Wrocław, Poland.
authors.forename: Teresa
authors.initials: T
authors.lastname: Olejniczak
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Mironowicz
authors.forename: Czesław
authors.initials: C
authors.lastname: Wawrzeńczyk
mesh_terms: D001711:Biotransformation; D004952:Esters / Q000378:metabolism*; D005638:Fruit / Q000201:enzymology / Q000378:metabolism*; D006368:Helianthus / Q000201:enzymology / Q000378:metabolism*; D006863:Hydrogen-Ion Concentration; D007783:Lactones / Q000378:metabolism*; D027845:Malus / Q000201:enzymology / Q000378:metabolism*
chemical_list: D004952:Esters; D007783:Lactones