Efficient laccase/TEMPO oxidation of alkyl glycosides: Effects of carbohydrate group and alkyl chain length

Abstract

Alkyl glycosides with long hydrophobic chains have attractive surfactant properties, but their wider application is hampered by their low solubility in water. Here, a route to increased solubility by introduction of carboxyl groups via laccase/TEMPO oxidation is presented. The oxidation pathways for dodecyl β-maltoside and hexadecyl β-maltoside were studied in detail. Close to full conversion was achieved for both substrates and conditions were found under which the diacid products dominated, with only minor amounts of under-oxidized and over-oxidized products. Dodecyl β-maltoside oxidation was improved to give a yield of 85 % of the diacid derivative. Interestingly, in spite of low substrate solubility the oxidation of hexadecyl β-maltoside was very efficient in aqueous medium, due to the higher solubility of the products. Addition of organic cosolvents did not provide additional advantages. The method is promising for producing soluble anionic derivatives of alkyl glycosides in an environmentally friendly and efficient way.