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Product profiles in enzymic and non-enzymic oxidations of the lignin model compound erythro-1-(3,4-dimethoxyphenyl)2-(2-methoxyphenoxy)-1,3-propanediol

Bohlin, C; Persson, P; Gorton, Lo LU ; Lundquist, K and Jonsson, LF (2005) In Journal of Molecular Catalysis B: Enzymatic 35(4-6). p.100-107
Abstract
The erythro form of the lignin model compound 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)-1,3-propanediol (1) was oxidized with laccase/ABTS, lead(IV) tetraacetate (LTA), lignin peroxidase/H2O2, cerium(IV) ammonium nitrate (CAN) and Fenton's reagent. The product profiles obtained with the different oxidants were compared after separation, identification and quantification of the products using HPLC, UV-diode array detector and electrospray ionization mass spectrometry in positive ionization mode. The oxidants generated different product profiles that reflected their different properties. Oxidation with laccase/ABTS resulted almost exclusively in formation of 1-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)-1- propanone (2).... (More)
The erythro form of the lignin model compound 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)-1,3-propanediol (1) was oxidized with laccase/ABTS, lead(IV) tetraacetate (LTA), lignin peroxidase/H2O2, cerium(IV) ammonium nitrate (CAN) and Fenton's reagent. The product profiles obtained with the different oxidants were compared after separation, identification and quantification of the products using HPLC, UV-diode array detector and electrospray ionization mass spectrometry in positive ionization mode. The oxidants generated different product profiles that reflected their different properties. Oxidation with laccase/ABTS resulted almost exclusively in formation of 1-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)-1- propanone (2). Oxidation with LTA resulted in more 3,4-dimethoxybenzaldehyde (3) than ketone 2. Lignin peroxidase and CAN gave similar product profiles and aldehyde 3 was the predominant product (only small amounts of ketone 2 were formed). Oxidation with Fenton's reagent resulted in the formation of more aldehyde 3 than ketone 2 but the yields were very low. CAN served as an excellent model for the lignin peroxidase-catalyzed oxidation, while the laccase-mediator system, LTA and Fenton's reagent provided distinctly different product profiles. Erythro-1-(3,4-dimethoxyphenyl)-1,2,3-propanetriol was present among the products obtained on oxidation with LTA, lignin peroxidase, CAN and Fenton's reagent. The differences in redox potential between the oxidants afford an explanation of the diverse product patterns but other factors may also be of importance. The reactions leading to cleavage of the P-ether bond with formation of 1-(3,4-dimethoxyphenyl)-1,2,3-propanetriol (veratryl glycerol) were found to proceed without affecting the configuration at the P-carbon atom. (c) 2005 Elsevier B.V. All rights reserved. (Less)
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type
Contribution to journal
publication status
published
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in
Journal of Molecular Catalysis B: Enzymatic
volume
35
issue
4-6
pages
100 - 107
publisher
Elsevier
external identifiers
  • wos:000231780400004
  • scopus:27644551038
ISSN
1873-3158
DOI
10.1016/j.molcatb.2005.06.003
language
English
LU publication?
yes
id
28a09531-a444-4c99-99f0-966a85c4b4c3 (old id 150964)
date added to LUP
2007-06-26 13:03:51
date last changed
2017-09-17 04:49:12
@article{28a09531-a444-4c99-99f0-966a85c4b4c3,
  abstract     = {The erythro form of the lignin model compound 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)-1,3-propanediol (1) was oxidized with laccase/ABTS, lead(IV) tetraacetate (LTA), lignin peroxidase/H2O2, cerium(IV) ammonium nitrate (CAN) and Fenton's reagent. The product profiles obtained with the different oxidants were compared after separation, identification and quantification of the products using HPLC, UV-diode array detector and electrospray ionization mass spectrometry in positive ionization mode. The oxidants generated different product profiles that reflected their different properties. Oxidation with laccase/ABTS resulted almost exclusively in formation of 1-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)-1- propanone (2). Oxidation with LTA resulted in more 3,4-dimethoxybenzaldehyde (3) than ketone 2. Lignin peroxidase and CAN gave similar product profiles and aldehyde 3 was the predominant product (only small amounts of ketone 2 were formed). Oxidation with Fenton's reagent resulted in the formation of more aldehyde 3 than ketone 2 but the yields were very low. CAN served as an excellent model for the lignin peroxidase-catalyzed oxidation, while the laccase-mediator system, LTA and Fenton's reagent provided distinctly different product profiles. Erythro-1-(3,4-dimethoxyphenyl)-1,2,3-propanetriol was present among the products obtained on oxidation with LTA, lignin peroxidase, CAN and Fenton's reagent. The differences in redox potential between the oxidants afford an explanation of the diverse product patterns but other factors may also be of importance. The reactions leading to cleavage of the P-ether bond with formation of 1-(3,4-dimethoxyphenyl)-1,2,3-propanetriol (veratryl glycerol) were found to proceed without affecting the configuration at the P-carbon atom. (c) 2005 Elsevier B.V. All rights reserved.},
  author       = {Bohlin, C and Persson, P and Gorton, Lo and Lundquist, K and Jonsson, LF},
  issn         = {1873-3158},
  language     = {eng},
  number       = {4-6},
  pages        = {100--107},
  publisher    = {Elsevier},
  series       = {Journal of Molecular Catalysis B: Enzymatic},
  title        = {Product profiles in enzymic and non-enzymic oxidations of the lignin model compound erythro-1-(3,4-dimethoxyphenyl)2-(2-methoxyphenoxy)-1,3-propanediol},
  url          = {http://dx.doi.org/10.1016/j.molcatb.2005.06.003},
  volume       = {35},
  year         = {2005},
}