N-Geranylated Amino Acid Surfactants with Low Critical Micelle Concentrations from Abundant, Naturally Derived Starting Materials

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dc.contributor.authorPollard, Brett L.en
dc.contributor.authorLiu, Yumengen
dc.contributor.authorGardiner, Michael G.en
dc.contributor.authorConnal, Luke A.en
dc.date.accessioned2026-02-25T17:41:08Z
dc.date.available2026-02-25T17:41:08Z
dc.date.issued2025en
dc.description.abstractIn this work, a simple method for the preparation of N-alkylated amino acid surfactants in 1–2 steps is reported. These products perform comparably to existing ionic surfactants, with N-tetrahydrogeranylated serine having a critical micelle concentration (CMC) of only 7.4 mmol·L−1. The suite of multiply charged surfactants generally possesses CMCs comparable to existing ionic surfactants. Further, their synthesis is simple, high-yielding, scalable, and does not require complex purification. The most hydrophobic surfactant (N-geranylated glycine) was found to have a log n-octanol-water partition coefficient (Pow) of 1.6 (indicating low bioaccumulative potential), and a single-step product (N-geranylated aspartic acid) was assessed for detergency potential via swatch testing.en
dc.description.sponsorshipB.L.P. and Y.L. contributed equally to this work. This work was graciously supported by the Australian Research Council and the grant ID is DP230100679. Prof. Vincent Craig assisted in accessing the surface tensiometer instrument, Douglas Lawes assisted with addressing NMR spectroscopy issues and Sandra Jestin offered the use of her camera for imaging. Open access publishing facilitated by Australian National University, as part of the Wiley - Australian National University agreement via the Council of Australian University Librarians. B.L.P. and Y.L. contributed equally to this work. This work was graciously supported by the Australian Research Council and the grant ID is DP230100679. Prof. Vincent Craig assisted in accessing the surface tensiometer instrument, Douglas Lawes assisted with addressing NMR spectroscopy issues and Sandra Jestin offered the use of her camera for imaging.en
dc.description.statusPeer-revieweden
dc.format.extent8en
dc.identifier.otherWOS:001554646400001en
dc.identifier.otherPubMed:40842216en
dc.identifier.otherORCID:/0000-0001-7519-977X/work/206443766en
dc.identifier.scopus105013673637en
dc.identifier.urihttps://hdl.handle.net/1885/733806584
dc.language.isoenen
dc.provenanceThis is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.en
dc.rights © 2025 The Author(s).en
dc.sourceChemistryOpenen
dc.subjectaldehydesen
dc.subjectamino acidsen
dc.subjectmicellesen
dc.subjectsurfactantsen
dc.subjectsustainable chemistryen
dc.titleN-Geranylated Amino Acid Surfactants with Low Critical Micelle Concentrations from Abundant, Naturally Derived Starting Materialsen
dc.typeJournal articleen
dspace.entity.typePublicationen
local.contributor.affiliationPollard, Brett L.; The Australian National Universityen
local.contributor.affiliationLiu, Yumeng; Australian National Universityen
local.contributor.affiliationGardiner, Michael G.; The Australian National Universityen
local.contributor.affiliationConnal, Luke A.; The Australian National Universityen
local.identifier.citationvolume14en
local.identifier.doi10.1002/open.202500421en
local.identifier.pure426f745a-521b-4d28-95a7-c08d4002c8d1en
local.identifier.urlhttps://www.scopus.com/pages/publications/105013673637en
local.type.statusPublisheden

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