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.

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

Semproli, Riccardo
Investigation
;
Simona Robescu, Marina
Investigation
;
Bavaro, Teodora
Data Curation
;
Ubiali, Daniela
Conceptualization
2023-01-01

Abstract

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.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11571/1469066
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