4.5 Article

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

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CHEMPLUSCHEM
卷 88, 期 1, 页码 -

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WILEY-V C H VERLAG GMBH
DOI: 10.1002/cplu.202200331

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biocatalysis; biosurfactants; emulsifiers; lactose; sugar fatty acid esters

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A library of alkyl galactosides synthesized as non-ionic surfactants showed that esters of galactopyranosides are superior to those of galactofuranosides in terms of interfacial tension and emulsifying properties. The enantiopure n-butyl 6-O-palmitoyl-beta-D-galactoside, prepared by the fully enzymatic route, led to the most stable emulsion. These findings suggest the potential use of lactose-rich cheese whey to obtain bio-based surfactants.
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 beta-D-galactopyranosides, whereas the Fischer glycosylation of galactose afforded isomeric mixtures of alpha- and beta-galactopyranosides and alpha- and beta-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-beta-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.

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