From Lactose to Alkyl Galactoside Fatty Acid Esters as Non-Ionic Biosurfactants: A Two-Step Enzymatic Approach to Cheese Whey Valorization.

Autor: Semproli R; Department of Drug Sciences, University of Pavia, Viale Taramelli 12, Pavia, I-27100, Italy., Simona Robescu M; Department of Drug Sciences, University of Pavia, Viale Taramelli 12, Pavia, I-27100, Italy., Sangiorgio S; Department of Chemistry, University of Milano, Via Golgi 19, Milano, I-20133, Italy., Pargoletti E; Department of Chemistry, University of Milano, Via Golgi 19, Milano, I-20133, Italy., Bavaro T; Department of Drug Sciences, University of Pavia, Viale Taramelli 12, Pavia, I-27100, Italy., Rabuffetti M; Department of Chemistry, University of Milano, Via Golgi 19, Milano, I-20133, Italy., Cappelletti G; Department of Chemistry, University of Milano, Via Golgi 19, Milano, I-20133, Italy., Speranza G; Department of Chemistry, University of Milano, Via Golgi 19, Milano, I-20133, Italy., Ubiali D; Department of Drug Sciences, University of Pavia, Viale Taramelli 12, Pavia, I-27100, Italy.
Jazyk: angličtina
Zdroj: ChemPlusChem [Chempluschem] 2023 Jan; Vol. 88 (1), pp. e202200331.
DOI: 10.1002/cplu.202200331
Abstrakt: A library of alkyl galactosides was synthesized to provide the "polar head" of sugar fatty acid esters to be tested as non-ionic surfactants. The enzymatic transglycosylation of lactose resulted in alkyl β-D-galactopyranosides, whereas the Fischer glycosylation of galactose afforded isomeric mixtures of α- and β-galactopyranosides and α- and β-galactofuranosides. n-Butyl galactosides from either routes were enzymatically esterified with palmitic acid, used as the fatty acid "tail" of the surfactant, giving the corresponding n-butyl 6-O-palmitoyl-galactosides. Measurements of interfacial tension and emulsifying properties of n-butyl 6-O-palmitoyl-galactosides revealed that the esters of galactopyranosides are superior to those of galactofuranosides, and that the enantiopure n-butyl 6-O-palmitoyl-β-D-galactoside, prepared by the fully enzymatic route, leads to the most stable emulsion. These results pave the way to the use of lactose-rich cheese whey as raw material for the obtainment of bio-based surfactants.
(© 2022 Wiley-VCH GmbH.)
Databáze: MEDLINE
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