Supported ionic liquid phase facilitated catalysis with lipase from Aspergillus oryzae for enhance enantiomeric resolution of racemic ibuprofen

Wolny, A; Siewniak, A; Zdarta, J; Ciesielczyk, F; Latos, P; Jurczyk, S; Nghiem, LD; Jesionowski, T; Chrobok, A

Supported ionic liquid phase facilitated catalysis with lipase from Aspergillus oryzae for enhance enantiomeric resolution of racemic ibuprofen

Wolny, A Siewniak, A Zdarta, J Ciesielczyk, F Latos, P Jurczyk, S Nghiem, LD Jesionowski, T Chrobok, A

Permalink

Publisher:: Elsevier
Publication Type:: Journal Article
Citation:: Environmental Technology and Innovation, 2022, 28, pp. 102936
Issue Date:: 2022-11-01

Open Access

Copyright Clearance Process

Recently Added
In Progress
Open Access

This item is open access.

Adobe PDF

Download Published versionAdobe PDF (952.36 kB)

View on publisher's site

View statistics

Full metadata record

Field	Value	Language
dc.contributor.author	Wolny, A
dc.contributor.author	Siewniak, A
dc.contributor.author	Zdarta, J
dc.contributor.author	Ciesielczyk, F
dc.contributor.author	Latos, P
dc.contributor.author	Jurczyk, S
dc.contributor.author	Nghiem, LD
dc.contributor.author	Jesionowski, T
dc.contributor.author	Chrobok, A
dc.date.accessioned	2023-07-10T05:15:53Z
dc.date.available	2023-07-10T05:15:53Z
dc.date.issued	2022-11-01
dc.identifier.citation	Environmental Technology and Innovation, 2022, 28, pp. 102936
dc.identifier.issn	2352-1864
dc.identifier.issn	2352-1864
dc.identifier.uri	http://hdl.handle.net/10453/171400
dc.description.abstract	Supported ionic liquid phase (SILP) was used as a carrier for lipase from Aspergillus oryzae (LAO) and used as a biocatalyst for enantiomeric resolution of racemic ibuprofen via esterification leading to (S)-(+)-ibuprofen ester. Using native form of lipase, outstanding results were achieved, obtaining (S)-(+)-ibuprofen propyl ester with enantiomeric excess (ee) of 99.9% and high conversion of racemic ibuprofen after 24 h (α=34.8%) and respectively ee = 99.9% with α=45.2% after 48 h. Several hybrid materials composited with silica and metal-based oxides including magnesium, calcium, and zirconia were evaluated as supports for LAO with various surface characteristics. The selected ionic liquid 1-methyl-3-(triethoxysilylpropyl)imidazolium bis(trifluoromethylsulfonyl)imide was immobilized via the covalent bound onto the surface of solid material and in the second step LAO was anchored. Optimized results in enantiomeric resolution of racemic ibuprofen (35.23% conversion of rac-ibuprofen after 7 days with 95% ee of ester) were obtained for SILP biocatalyst based on MgO⋅ SiO2 (1:1) (ionic liquid loading 6.79%, enzyme loading 3.96%). This is proposed as a generic approach to tailoring supported ionic liquids phase biocatalysts for industrially-relevant reactions, to generate both environmentally and economically sustainable processes.
dc.language	en
dc.publisher	Elsevier
dc.relation.ispartof	Environmental Technology and Innovation
dc.relation.isbasedon	10.1016/j.eti.2022.102936
dc.rights	info:eu-repo/semantics/openAccess
dc.subject	0502 Environmental Science and Management, 0907 Environmental Engineering, 1002 Environmental Biotechnology
dc.title	Supported ionic liquid phase facilitated catalysis with lipase from Aspergillus oryzae for enhance enantiomeric resolution of racemic ibuprofen
dc.type	Journal Article
utslib.citation.volume	28
utslib.for	0502 Environmental Science and Management
utslib.for	0907 Environmental Engineering
utslib.for	1002 Environmental Biotechnology
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Engineering and Information Technology
pubs.organisational-group	/University of Technology Sydney/Faculty of Engineering and Information Technology/School of Civil and Environmental Engineering
pubs.organisational-group	/University of Technology Sydney/Strength - CTWW - Centre for Technology in Water and Wastewater Treatment
utslib.copyright.status	open_access	*
dc.date.updated	2023-07-10T05:15:52Z
pubs.publication-status	Published
pubs.volume	28

Abstract:

Supported ionic liquid phase (SILP) was used as a carrier for lipase from Aspergillus oryzae (LAO) and used as a biocatalyst for enantiomeric resolution of racemic ibuprofen via esterification leading to (S)-(+)-ibuprofen ester. Using native form of lipase, outstanding results were achieved, obtaining (S)-(+)-ibuprofen propyl ester with enantiomeric excess (ee) of 99.9% and high conversion of racemic ibuprofen after 24 h (α=34.8%) and respectively ee = 99.9% with α=45.2% after 48 h. Several hybrid materials composited with silica and metal-based oxides including magnesium, calcium, and zirconia were evaluated as supports for LAO with various surface characteristics. The selected ionic liquid 1-methyl-3-(triethoxysilylpropyl)imidazolium bis(trifluoromethylsulfonyl)imide was immobilized via the covalent bound onto the surface of solid material and in the second step LAO was anchored. Optimized results in enantiomeric resolution of racemic ibuprofen (35.23% conversion of rac-ibuprofen after 7 days with 95% ee of ester) were obtained for SILP biocatalyst based on MgO⋅ SiO2 (1:1) (ionic liquid loading 6.79%, enzyme loading 3.96%). This is proposed as a generic approach to tailoring supported ionic liquids phase biocatalysts for industrially-relevant reactions, to generate both environmentally and economically sustainable processes.

Please use this identifier to cite or link to this item:

http://hdl.handle.net/10453/171400