Deuterated squalene and sterols from modified Saccharomyces cerevisiae

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dc.contributor.authorRecsei, Cen_AU
dc.contributor.authorRussell, RAen_AU
dc.contributor.authorCagnes, MPen_AU
dc.contributor.authorDarwish, TAen_AU
dc.date.accessioned2024-02-23T00:46:04Zen_AU
dc.date.available2024-02-23T00:46:04Zen_AU
dc.date.issued2023-07-31en_AU
dc.date.statistics2024-02-23en_AU
dc.description.abstractUniformly deuterated sterols and biosynthetically related materials are important for neutron, NMR, tracing and bioanalysis studies as well as critical tools for the creation of improved lipid nanoparticle formulations. The production of sufficient quantities of materials relies not only on the engineering of microorganisms to selectively accumulate desired materials but also methods for the isolation, purification and characterisation of these materials to ensure their usefulness. Uniformly deuterated squalene, the universal precursor to sterols in biological systems, has been produced and characterised. Cholesterol has been produced with controlled levels of uniform deuteration, increased biosynthetic yield and a methodology developed for the extraction and purification of this material without HPLC. Two sterols, not previously produced in deuterated forms, have been prepared with uniform deuteration: 22,23-dihydrobrassicasterol and 24-methylenecholesterol. This report triples the number of sterols that have been produced with uniform deuteration, purified and characterised and provides a silylation/silver ion chromatography protocol for the separation of sterols which differ by the degree of unsaturation. The techniques for the 13C NMR analysis of deuterated sterols, site-specific deuteration levels and an analysis of key biosynthetic steps based on these data are reported. © 2023 The Royal Society of Chemistry, Open Access, published under a CC-BY-NC licence.en_AU
dc.description.sponsorshipThe National Deuteration Facility is partly supported by the National Collaborative Research Infrastructure Strategy – an initiative of the Australian Government. The authors gratefully acknowledge the provision of S. cerevisiae strains Y2805 by Dr Eui-Sung Choi and RH6827 and RH6829 by Emeritus Professor Howard Riezman.en_AU
dc.format.mediumElectronicen_AU
dc.identifier.citationRecsei, C., Russell, R. A., Cagnes, M., & Darwish, T. (2023). Deuterated squalene and sterols from modified Saccharomyces cerevisiae. Organic & Biomolecular Chemistry, 21(32), 6537-6548. doi:10.1039/d3ob00754een_AU
dc.identifier.issn1477-0520en_AU
dc.identifier.issn1477-0539en_AU
dc.identifier.issue32en_AU
dc.identifier.journaltitleOrganic & Biomolecular Chemistryen_AU
dc.identifier.pagination6537-6548en_AU
dc.identifier.urihttp://dx.doi.org/10.1039/d3ob00754een_AU
dc.identifier.urihttps://apo.ansto.gov.au/handle/10238/15407en_AU
dc.identifier.volume21en_AU
dc.languageEnglishen_AU
dc.language.isoenen_AU
dc.publisherRoyal Society of Chemistry (RSC)en_AU
dc.subjectDeuterationen_AU
dc.subjectSqualeneen_AU
dc.subjectSterolsen_AU
dc.subjectYeastsen_AU
dc.subjectMicroorganismsen_AU
dc.subjectLipidsen_AU
dc.titleDeuterated squalene and sterols from modified Saccharomyces cerevisiaeen_AU
dc.typeJournal Articleen_AU
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