Laccase catalysed modification of lignin subunits and coupling to p-aminobenzoic acid
(2013) In Journal of Molecular Catalysis B: Enzymatic 97. p.45-53- Abstract
- Laccase catalysed oxidation of syringyl and guaiacyl subunits of lignin and their modification with an aromatic amine, p-aminobenzoic acid (PABA) were investigated. Laccase from Galerina sp. HC1 isolated earlier by us was used as the main catalyst, and Trametes versicolor laccase was used for comparison. Among the syringyl compounds, syringic acid and syringaldehyde were oxidised to 2,6-dimethoxy-1,4-benzoquinone, and in the presence of PABA yielded a cross-coupling imine product. The reaction with methyl syringol resulted in several products whose structures were determined. The possible oxidative coupling pathways were proposed for the formation of the identified products. Oxidation of syringol and the guaiacyl compounds resulted mainly... (More)
- Laccase catalysed oxidation of syringyl and guaiacyl subunits of lignin and their modification with an aromatic amine, p-aminobenzoic acid (PABA) were investigated. Laccase from Galerina sp. HC1 isolated earlier by us was used as the main catalyst, and Trametes versicolor laccase was used for comparison. Among the syringyl compounds, syringic acid and syringaldehyde were oxidised to 2,6-dimethoxy-1,4-benzoquinone, and in the presence of PABA yielded a cross-coupling imine product. The reaction with methyl syringol resulted in several products whose structures were determined. The possible oxidative coupling pathways were proposed for the formation of the identified products. Oxidation of syringol and the guaiacyl compounds resulted mainly in homooligomers by free radical mechanism, with a negligible tendency of reaction with the nucleophilic group of PABA. Similar treatment of Eucalyptus Kraft lignin, which is rich in syringyl moieties, showed the presence of identical products obtained with syringic acid and syringaldehyde. (C) 2013 Elsevier B.V. All rights reserved. (Less)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/4196491
- author
- Ibrahim, Victor LU ; Volkova, Natalia LU ; Pyo, Sang-Hyun LU ; Mamo, Gashaw LU and Hatti-Kaul, Rajni LU
- organization
- publishing date
- 2013
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- Laccase, Syringyl subunits, Guaiacyl subunits, Oxidative coupling, pathways, Structure elucidation
- in
- Journal of Molecular Catalysis B: Enzymatic
- volume
- 97
- pages
- 45 - 53
- publisher
- Elsevier
- external identifiers
-
- wos:000327005000008
- scopus:84884508373
- ISSN
- 1873-3158
- DOI
- 10.1016/j.molcatb.2013.07.014
- language
- English
- LU publication?
- yes
- id
- 089af4de-5f6e-4dd1-a9a6-711b5e706330 (old id 4196491)
- date added to LUP
- 2016-04-01 10:38:55
- date last changed
- 2022-01-26 01:13:14
@article{089af4de-5f6e-4dd1-a9a6-711b5e706330, abstract = {{Laccase catalysed oxidation of syringyl and guaiacyl subunits of lignin and their modification with an aromatic amine, p-aminobenzoic acid (PABA) were investigated. Laccase from Galerina sp. HC1 isolated earlier by us was used as the main catalyst, and Trametes versicolor laccase was used for comparison. Among the syringyl compounds, syringic acid and syringaldehyde were oxidised to 2,6-dimethoxy-1,4-benzoquinone, and in the presence of PABA yielded a cross-coupling imine product. The reaction with methyl syringol resulted in several products whose structures were determined. The possible oxidative coupling pathways were proposed for the formation of the identified products. Oxidation of syringol and the guaiacyl compounds resulted mainly in homooligomers by free radical mechanism, with a negligible tendency of reaction with the nucleophilic group of PABA. Similar treatment of Eucalyptus Kraft lignin, which is rich in syringyl moieties, showed the presence of identical products obtained with syringic acid and syringaldehyde. (C) 2013 Elsevier B.V. All rights reserved.}}, author = {{Ibrahim, Victor and Volkova, Natalia and Pyo, Sang-Hyun and Mamo, Gashaw and Hatti-Kaul, Rajni}}, issn = {{1873-3158}}, keywords = {{Laccase; Syringyl subunits; Guaiacyl subunits; Oxidative coupling; pathways; Structure elucidation}}, language = {{eng}}, pages = {{45--53}}, publisher = {{Elsevier}}, series = {{Journal of Molecular Catalysis B: Enzymatic}}, title = {{Laccase catalysed modification of lignin subunits and coupling to p-aminobenzoic acid}}, url = {{http://dx.doi.org/10.1016/j.molcatb.2013.07.014}}, doi = {{10.1016/j.molcatb.2013.07.014}}, volume = {{97}}, year = {{2013}}, }