Multifactorial optimization enables the identification of a greener method to produce (+)-nootkatone

dc.contributor.authorMakhubela, Ida M.
dc.contributor.authorZawaira, Alexander
dc.contributor.authorBrady, Dean
dc.contributor.authorPienaar, Daniel P.
dc.contributor.emaildaniel.pienaar@up.ac.zaen_US
dc.date.accessioned2025-03-24T10:46:59Z
dc.date.available2025-03-24T10:46:59Z
dc.date.issued2024-09
dc.descriptionDATA AVAILABILITY : Data will be made available on request.en_US
dc.description.abstractThe natural aroma compound (+)-nootkatone was obtained in selective conversions of up to 74 mol% from inexpensive (+)-valencene substrate by using a comparatively greener biocatalytic process developed based on modifications of the previously published Firmenich method. Buffer identity and concentration, pH, temperature and downstream work-up procedures were optimized to produce a crude product in which >90 % of (+)-valencene had been converted, with high chemoselectivity observed for (+)-nootkatone production. Interestingly, the biotransformation was carried out efficiently at temperatures as low as 21 ºC. Surprisingly, the best results were obtained when an acidic pH in the range of 3–6 was applied, as compared to the previously published procedure in which it appeared to be necessary to buffer the pH optimally and fixed throughout at 8.5. Furthermore, there was no need to maintain a pure oxygen atmosphere to achieve good (+)-nootkatone yields. Instead, air bubbled continuously at a low rate through the reaction mixture via a submerged glass capillary was sufficient to enable the desired lipoxygenase-catalyzed oxidation reactions to occur efficiently. No valencene epoxide side-products were detected in the organic product extract by a standard GCMS protocol. Only traces of the anticipated corresponding α- and β-nootkatol intermediates were routinely observed.en_US
dc.description.departmentChemistryen_US
dc.description.librarianam2024en_US
dc.description.sdgSDG-02:Zero Hungeren_US
dc.description.sponsorshipThe Technology and Human Resources for Industry Program (THRIP), South Africa and the Department of Science and Innovation (DSI), South Africa, Biocatalysis Initiative, that includes the DSI Industrial Biocatalysis Hub.en_US
dc.description.urihttp://www.elsevier.com/locate/jbiotecen_US
dc.identifier.citationMakhubela, I.M., Zawaira, A., Brady, D et al. 2024, 'Multifactorial optimization enables the identification of a greener method to produce (+)-nootkatone', Journal of Biotechnology, vol. 393, pp. 41-48. https://DOI.org/10.1016/j.jbiotec.2024.07.008.en_US
dc.identifier.issn0168-1656 (print)
dc.identifier.issn1873-4863 (online)
dc.identifier.other10.1016/j.jbiotec.2024.07.008
dc.identifier.urihttp://hdl.handle.net/2263/101657
dc.language.isoenen_US
dc.publisherElsevieren_US
dc.rights© 2024 The Author(s). This is an open access article under the CC BY-NC license.en_US
dc.subjectNootkatoneen_US
dc.subjectSoy bean lipoxygenaseen_US
dc.subjectBiocatalysisen_US
dc.subjectGreen processen_US
dc.subjectSDG-02: Zero hungeren_US
dc.titleMultifactorial optimization enables the identification of a greener method to produce (+)-nootkatoneen_US
dc.typeArticleen_US

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