Chemoenzymatic synthesis of the pH responsive surfactant octyl β-D-glucopyranoside uronic acid
(2020) In Applied Microbiology and Biotechnology 104. p.1055-1062- 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... (More)
- 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). (Less)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/b18063de-ae89-421f-af25-d04a15f2fb8d
- author
- NGO, NGOC LU ; Grey, Carl LU and Adlercreutz, Patrick LU
- organization
- publishing date
- 2020
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- Oxidation, octyl β-D-glucopyranoside, octyl β-D-glucopyranoside uronic acid, laccase from Trametes versicolor, TEMPO, foam
- in
- Applied Microbiology and Biotechnology
- volume
- 104
- pages
- 8 pages
- publisher
- Springer
- external identifiers
-
- scopus:85076297687
- pmid:31811319
- ISSN
- 1432-0614
- DOI
- 10.1007/s00253-019-10254-x
- language
- English
- LU publication?
- yes
- id
- b18063de-ae89-421f-af25-d04a15f2fb8d
- date added to LUP
- 2020-09-03 16:27:58
- date last changed
- 2022-04-19 00:28:54
@article{b18063de-ae89-421f-af25-d04a15f2fb8d, 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 <i>T. versicolor laccase</i>/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).}}, author = {{NGO, NGOC and Grey, Carl and Adlercreutz, Patrick}}, issn = {{1432-0614}}, keywords = {{Oxidation; octyl β-D-glucopyranoside; octyl β-D-glucopyranoside uronic acid; laccase from Trametes versicolor; TEMPO; foam}}, language = {{eng}}, pages = {{1055--1062}}, publisher = {{Springer}}, series = {{Applied Microbiology and Biotechnology}}, title = {{Chemoenzymatic synthesis of the pH responsive surfactant octyl β-D-glucopyranoside uronic acid}}, url = {{https://lup.lub.lu.se/search/files/83390877/Ngoc_Ngo_Octyl_glucoside_oxidation.pdf}}, doi = {{10.1007/s00253-019-10254-x}}, volume = {{104}}, year = {{2020}}, }