Chemoenzymatic synthesis of the pH responsive surfactant octyl β-D-glucopyranoside uronic acid

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Abstract

Methodology was developed to expand the range of benign alkyl glycoside surfactants to include also anionic types. This was demonstrated possible through conversion of the glycoside to its carboxyl derivative. Specifically, octyl β-D-glucopyranoside (OG) was oxidized to the corresponding uronic acid (octyl β-D-glucopyranoside uronic acid, OG-COOH) using the catalyst system T. versicolor laccase/2,2,6,6-tetramethylpiperidinyloxy (TEMPO) and oxygen from air as oxidant. The effects of oxygen supply methodology, concentrations of laccase, TEMPO and OG as well as reaction temperature were evaluated. At 10 mM substrate concentration, the substrate was almost quantitatively converted into product and even at a substrate concentration of 60 mM, 85 % conversion was reached within 24 hours. The surfactant properties of OG-COOH were markedly dependent on pH. Foaming was only observed at low pH, while no foam was formed at pH values above 5.0. Thus, OG-COOH can be an attractive low-foaming surfactant, for example for cleaning applications and emulsification, in a wide pH range (pH 1.5-10.0).

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Subject classification (UKÄ) – MANDATORY

  • Biocatalysis and Enzyme Technology

Keywords

  • Oxidation, octyl β-D-glucopyranoside, octyl β-D-glucopyranoside uronic acid, laccase from Trametes versicolor, TEMPO, foam
Original languageEnglish
Pages (from-to)1055-1062
Number of pages8
JournalApplied Microbiology and Biotechnology
Volume104
Publication statusPublished - 2020
Publication categoryResearch
Peer-reviewedYes

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