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Vegetables as biocatalysts in stereoselective hydrolysis of labile organic compounds
University of Kalmar, School of Pure and Applied Natural Sciences.
University of Kalmar, School of Pure and Applied Natural Sciences.
University of Kalmar, School of Pure and Applied Natural Sciences.ORCID iD: 0000-0001-7158-6393
2009 (English)In: Green Chemistry, ISSN 1463-9262, E-ISSN 1463-9270, Vol. 11, no 11, p. 1900-1905Article in journal (Refereed) Published
Abstract [en]

Hydrolysis of labile esters of beta-hydroxyketones has been performed with whole plant tissue from various vegetables. The pheromone 5-hydroxy-4-methyl-3-heptanone (1) was used as the model compound. Hydrolysis of acetates and benzoates of 1 was unsuccessful using normal conditions of ester hydrolysis, both by chemical hydrolysis and by the means of commercial lipases. When, however, whole cells of carrot, celery root, eggplant, parsley root, parsnip and potato were used as reagents, hydrolysis of the acetates was successful. At low conversion the hydrolysis was stereoselective and at total conversion virtually no formation of by-products was observed. The selectivity varied among the eight vegetables that were evaluated. Methods of preparation and substrate-to-plant ratio were examined. Furthermore, acetates and benzoates of three analogous compounds [5-hydroxy-3-heptanone (2), 5-hydroxy-5-methyl-3-heptanone (3) and 5-ethyl-6-hydroxy-4-octanone (4)] were hydrolyzed by potato and sweet potato to various degrees, indicating that the method is general for the mild and stereoselective hydrolysis of secondary beta-alkoxy-and beta-aryloxyketones.

Place, publisher, year, edition, pages
2009. Vol. 11, no 11, p. 1900-1905
National Category
Organic Chemistry
Research subject
Natural Science, Organic Chemistry; Natural Science
Identifiers
URN: urn:nbn:se:lnu:diva-2124DOI: 10.1039/B913936BOAI: oai:DiVA.org:lnu-2124DiVA, id: diva2:309174
Available from: 2010-04-06 Created: 2010-04-06 Last updated: 2017-12-12Bibliographically approved

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Bohman, BjörnUnelius, C. Rikard

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