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Improved Alkyl Glycoside Synthesis by trans-Glycosylation through Tailored Microenvironments of Immobilized β-Glucosidase

Hoffmann, Christian ; Grey, Carl LU orcid ; Pinelo, Manuel ; Woodley, John M. ; Daugaard, Anders E. and Adlercreutz, Patrick LU orcid (2020) In ChemPlusChem 85(1). p.137-141
Abstract

We present how the microenvironment can directly improve biocatalytic selectivity of immobilized β-glucosidase. β-Glucosidase from Thermotoga neapolitana was immobilized on a variety of functionalized off-stoichiometric thiol-ene (OSTE) particles, where highest activities were observed for thiol and imidazole functional particles. Compared to the soluble enzyme, the selectivity (rs/rh) between trans-glycosylation of p-nitrophenyl β-D-glucopyranoside (pNPG) with 1-propanol over hydrolysis was increased by a factor of 2–3 using particles containing imidazole (rs/rh of 6.7) and carboxylic acid moieties (rs/rh of 9.2), respectively. These results demonstrate clearly that... (More)

We present how the microenvironment can directly improve biocatalytic selectivity of immobilized β-glucosidase. β-Glucosidase from Thermotoga neapolitana was immobilized on a variety of functionalized off-stoichiometric thiol-ene (OSTE) particles, where highest activities were observed for thiol and imidazole functional particles. Compared to the soluble enzyme, the selectivity (rs/rh) between trans-glycosylation of p-nitrophenyl β-D-glucopyranoside (pNPG) with 1-propanol over hydrolysis was increased by a factor of 2–3 using particles containing imidazole (rs/rh of 6.7) and carboxylic acid moieties (rs/rh of 9.2), respectively. These results demonstrate clearly that enzyme selectivity depends directly on the local environment of the enzyme with the support.

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author
; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
alkyl glycosides, enzyme immobilization, hydrolases, surface functionalization, trans-glycosylation
in
ChemPlusChem
volume
85
issue
1
pages
5 pages
publisher
Institute of Organic Chemistry and Biochemistry
external identifiers
  • scopus:85079363126
ISSN
2192-6506
DOI
10.1002/cplu.201900680
language
English
LU publication?
yes
id
f0af92da-e0ef-41c0-99ab-eb8730c11f42
date added to LUP
2020-02-28 11:22:18
date last changed
2025-10-14 09:46:22
@article{f0af92da-e0ef-41c0-99ab-eb8730c11f42,
  abstract     = {{<p>We present how the microenvironment can directly improve biocatalytic selectivity of immobilized β-glucosidase. β-Glucosidase from Thermotoga neapolitana was immobilized on a variety of functionalized off-stoichiometric thiol-ene (OSTE) particles, where highest activities were observed for thiol and imidazole functional particles. Compared to the soluble enzyme, the selectivity (r<sub>s</sub>/r<sub>h</sub>) between trans-glycosylation of p-nitrophenyl β-D-glucopyranoside (pNPG) with 1-propanol over hydrolysis was increased by a factor of 2–3 using particles containing imidazole (r<sub>s</sub>/r<sub>h</sub> of 6.7) and carboxylic acid moieties (r<sub>s</sub>/r<sub>h</sub> of 9.2), respectively. These results demonstrate clearly that enzyme selectivity depends directly on the local environment of the enzyme with the support.</p>}},
  author       = {{Hoffmann, Christian and Grey, Carl and Pinelo, Manuel and Woodley, John M. and Daugaard, Anders E. and Adlercreutz, Patrick}},
  issn         = {{2192-6506}},
  keywords     = {{alkyl glycosides; enzyme immobilization; hydrolases; surface functionalization; trans-glycosylation}},
  language     = {{eng}},
  number       = {{1}},
  pages        = {{137--141}},
  publisher    = {{Institute of Organic Chemistry and Biochemistry}},
  series       = {{ChemPlusChem}},
  title        = {{Improved Alkyl Glycoside Synthesis by trans-Glycosylation through Tailored Microenvironments of Immobilized β-Glucosidase}},
  url          = {{http://dx.doi.org/10.1002/cplu.201900680}},
  doi          = {{10.1002/cplu.201900680}},
  volume       = {{85}},
  year         = {{2020}},
}