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

NGO, NGOC LU ; Grey, Carl LU and Adlercreutz, Patrick LU orcid (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)
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author
; and
organization
publishing date
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}},
}