From Lactose to Alkyl Galactoside Fatty Acid Esters as Non-Ionic Biosurfactants: A Two-Step Enzymatic Approach to Cheese Whey Valorization.
biocatalysis
biosurfactants
emulsifiers
lactose
sugar fatty acid esters
Journal
ChemPlusChem
ISSN: 2192-6506
Titre abrégé: Chempluschem
Pays: Germany
ID NLM: 101580948
Informations de publication
Date de publication:
01 2023
01 2023
Historique:
revised:
08
12
2022
received:
26
09
2022
entrez:
2
1
2023
pubmed:
3
1
2023
medline:
4
1
2023
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 36592040
doi: 10.1002/cplu.202200331
doi:
Substances chimiques
Lactose
J2B2A4N98G
Galactosides
0
Surface-Active Agents
0
Fatty Acids
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202200331Informations de copyright
© 2022 Wiley-VCH GmbH.
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