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Lipase-Mediated Mechanoenzymatic Synthesis of Sugar Esters in Dissolved Unconventional and Neat Reaction Systems

Hollenbach, Rebecca 1; Delavault, André 1; Gebhardt, Laura 1; Soergel, Hannah 2,3; Muhle-Goll, Claudia ORCID iD icon 2,3; Ochsenreither, Katrin ORCID iD icon 1; Syldatk, Christoph 1
1 Institut für Bio- und Lebensmitteltechnik (BLT), Karlsruher Institut für Technologie (KIT)
2 Institut für Biologische Grenzflächen (IBG), Karlsruher Institut für Technologie (KIT)
3 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)

Abstract (englisch):

Mechanochemical and biocatalytic approaches in modern research are two major assets to develop greener processes. In the present study, these modular tools of sustainability are pointed toward the production of versatile and daily employed compounds such as surfactants. Toward this aim, glycolipids, a class of nonionic surfactants composed of ubiquitous and primary metabolites such as sugar and fatty acid moieties, represent a promising alternative to petroleum-derived surface-active agents. Therefore, the combination of biocatalysis with mechanochemistry aiming at glycolipid synthesis seemed a logical step that was taken in this study for the first time. The monoacylated model compound glucose-6-O-decanoate was synthesized with the help of a bead mill apparatus using two different unconventional dissolved reaction systems, namely, menthol-based hydrophobic deep eutectic solvents and 2-methyl-2-butanol, thus reaching up to 12% yield in the latter based on the conversion of vinyl decanoate, after only 90 min of reaction. In addition, a neat reaction system using an excess of vinylated fatty ester as an adjuvant allowed a 27 mM/h space-time yield. ... mehr

DOI: 10.1021/acssuschemeng.2c01727
Zitationen: 8
Web of Science
Zitationen: 6
Zitationen: 7
Zugehörige Institution(en) am KIT Institut für Biologische Grenzflächen (IBG)
Institut für Bio- und Lebensmitteltechnik (BLT)
Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2022
Sprache Englisch
Identifikator ISSN: 2168-0485
KITopen-ID: 1000149429
HGF-Programm 43.35.02 (POF IV, LK 01) Functionality of Soft Matter and Biomolecular Systems
Erschienen in ACS Sustainable Chemistry & Engineering
Verlag American Chemical Society (ACS)
Band 10
Heft 31
Seiten 10192–10202
Vorab online veröffentlicht am 27.07.2022
Nachgewiesen in Web of Science
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