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Molecules 2017, 22(1), 147; doi:10.3390/molecules22010147

Synthesis and Biotransformation of Bicyclic Unsaturated Lactones with Three or Four Methyl Groups

1
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland
2
Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland
3
Institute of General Food Chemistry, Lodz University of Technology, Stefanowskiego 4/10, 90-924 Łódź, Poland
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 21 November 2016 / Revised: 4 January 2017 / Accepted: 11 January 2017 / Published: 17 January 2017
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Abstract

The aim of this study was to obtain new unsaturated lactones by chemical synthesis and their microbial transformations using fungal strains. Some of these strains were able to transform unsaturated lactones into different hydroxy or epoxy derivatives. Strains of Syncephalastrum racemosum and Absidia cylindrospora gave products with a hydroxy group introduced into a tertiary carbon, while the Penicillium vermiculatum strain hydroxylated primary carbons. The Syncephalastrum racemosum strain hydroxylated both substrates in an allylic position. Using the Absidia cylindrospora and Penicillium vermiculatum strains led to the obtained epoxylactones. The structures of all lactones were established on the basis of spectroscopic data. View Full-Text
Keywords: unsaturated lactones; hydroxylation; epoxidation; biotransformation unsaturated lactones; hydroxylation; epoxidation; biotransformation
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Wińska, K.; Grabarczyk, M.; Mączka, W.; Kondas, A.; Maciejewska, G.; Bonikowski, R.; Anioł, M. Synthesis and Biotransformation of Bicyclic Unsaturated Lactones with Three or Four Methyl Groups. Molecules 2017, 22, 147.

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