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.

From Lactose to Alkyl Galactoside Fatty Acid Esters as Non-Ionic Biosurfactants: A Two-Step Enzymatic Approach to Cheese Whey Valorization / R. Semproli, M. Simona Robescu, S. Sangiorgio, E. Pargoletti, T. Bavaro, M. Rabuffetti, G. Cappelletti, G. Speranza, D. Ubiali. - In: CHEMPLUSCHEM. - ISSN 2192-6506. - 88:1(2023 Jan), pp. e202200331.1-e202200331.9. [10.1002/cplu.202200331]

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

S. Sangiorgio;E. Pargoletti;M. Rabuffetti;G. Cappelletti;G. Speranza
Penultimo
;
2023

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 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.
biocatalysis; biosurfactants; emulsifiers; lactose; sugar fatty acid esters;
Settore CHIM/06 - Chimica Organica
Settore CHIM/02 - Chimica Fisica
   Integrated platform for the sustainable production of bio-based surfactants from renewable resources (BioSurf)
   BioSurf
   FONDAZIONE CARIPLO
   2020-1944
gen-2023
9-dic-2022
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/969117
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