Oxidation of lignans and lignin model compounds by laccase in aqueous solvent systems

Maija-Liisa Mattinen (Corresponding Author), P. Maijala, P. Nousiainen, A. Smeds, J. Kontro, J. Sipilä, Tarja Tamminen, S. Willför, Liisa Viikari

Research output: Contribution to journalArticleScientificpeer-review

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Abstract

The stability and activity of the low redox potential Melanocarpus albomyces laccase (MaL) in various aqueous organic (acetone, ethanol, propylene glycol, diethylene glycol monomethyl ether) solvent systems was studied spectrophotometrically using 2,6-dimethoxyphenol (2,6-DMP) as substrate. In addition, reactivity of the enzyme with two lignans; matairesinol (MR) and 7-hydroxymatairesinol (HMR), was examined by oxygen consumption measurements in the most potential aqueous organic solvent systems. Polymerization of the lignans by MaL was verified by matrix assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS) and size exclusion chromatography (SEC). Polymerization of the higher molecular weight lignin model compound, dehydrogenation polymers (DHPs), was studied by SEC. The solubilities of industrial softwood and hardwood kraft lignins were evaluated as parameters for investigation of enzymatic modification in aqueous organic solvent systems. The functioning of MaL in different aqueous organic media was excellent. Propylene glycol and diethylene glycol monomethyl ether were better solvents than ethanol or acetone in enzymatic oxidations. Even though they were the best solvents for enzyme oxidation, ethanol and propylene glycol were selected for further tests because of their different physicochemical properties. The results obtained in this study for the use of laccase-catalysed reactions in organic solvents to improve the efficiency of lignin oxidation may be exploited in several applications and areas in which the solubility of the reactants or products is a limiting factor.
Original languageEnglish
Pages (from-to)122-129
Number of pages8
JournalJournal of Molecular Catalysis B: Enzymatic
Volume72
Issue number3-4
DOIs
Publication statusPublished - 2011
MoE publication typeA1 Journal article-refereed

Fingerprint

Laccase
Lignans
Lignin
Glycols
Propylene Glycol
Organic solvents
Oxidation
Ethanol
Size exclusion chromatography
Propylene
Acetone
Solubility
Polymerization
Ethers
Enzymes
Gel Chromatography
Softwoods
Hardwoods
Dehydrogenation
Ionization

Keywords

  • Melanocarpus albomyces
  • laccase
  • solvent
  • reactivity
  • lignin
  • lignans
  • dehydrogenation polymers

Cite this

Mattinen, M-L., Maijala, P., Nousiainen, P., Smeds, A., Kontro, J., Sipilä, J., ... Viikari, L. (2011). Oxidation of lignans and lignin model compounds by laccase in aqueous solvent systems. Journal of Molecular Catalysis B: Enzymatic, 72(3-4), 122-129. https://doi.org/10.1016/j.molcatb.2011.05.009
Mattinen, Maija-Liisa ; Maijala, P. ; Nousiainen, P. ; Smeds, A. ; Kontro, J. ; Sipilä, J. ; Tamminen, Tarja ; Willför, S. ; Viikari, Liisa. / Oxidation of lignans and lignin model compounds by laccase in aqueous solvent systems. In: Journal of Molecular Catalysis B: Enzymatic. 2011 ; Vol. 72, No. 3-4. pp. 122-129.
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abstract = "The stability and activity of the low redox potential Melanocarpus albomyces laccase (MaL) in various aqueous organic (acetone, ethanol, propylene glycol, diethylene glycol monomethyl ether) solvent systems was studied spectrophotometrically using 2,6-dimethoxyphenol (2,6-DMP) as substrate. In addition, reactivity of the enzyme with two lignans; matairesinol (MR) and 7-hydroxymatairesinol (HMR), was examined by oxygen consumption measurements in the most potential aqueous organic solvent systems. Polymerization of the lignans by MaL was verified by matrix assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS) and size exclusion chromatography (SEC). Polymerization of the higher molecular weight lignin model compound, dehydrogenation polymers (DHPs), was studied by SEC. The solubilities of industrial softwood and hardwood kraft lignins were evaluated as parameters for investigation of enzymatic modification in aqueous organic solvent systems. The functioning of MaL in different aqueous organic media was excellent. Propylene glycol and diethylene glycol monomethyl ether were better solvents than ethanol or acetone in enzymatic oxidations. Even though they were the best solvents for enzyme oxidation, ethanol and propylene glycol were selected for further tests because of their different physicochemical properties. The results obtained in this study for the use of laccase-catalysed reactions in organic solvents to improve the efficiency of lignin oxidation may be exploited in several applications and areas in which the solubility of the reactants or products is a limiting factor.",
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Mattinen, M-L, Maijala, P, Nousiainen, P, Smeds, A, Kontro, J, Sipilä, J, Tamminen, T, Willför, S & Viikari, L 2011, 'Oxidation of lignans and lignin model compounds by laccase in aqueous solvent systems', Journal of Molecular Catalysis B: Enzymatic, vol. 72, no. 3-4, pp. 122-129. https://doi.org/10.1016/j.molcatb.2011.05.009

Oxidation of lignans and lignin model compounds by laccase in aqueous solvent systems. / Mattinen, Maija-Liisa (Corresponding Author); Maijala, P.; Nousiainen, P.; Smeds, A.; Kontro, J.; Sipilä, J.; Tamminen, Tarja; Willför, S.; Viikari, Liisa.

In: Journal of Molecular Catalysis B: Enzymatic, Vol. 72, No. 3-4, 2011, p. 122-129.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Oxidation of lignans and lignin model compounds by laccase in aqueous solvent systems

AU - Mattinen, Maija-Liisa

AU - Maijala, P.

AU - Nousiainen, P.

AU - Smeds, A.

AU - Kontro, J.

AU - Sipilä, J.

AU - Tamminen, Tarja

AU - Willför, S.

AU - Viikari, Liisa

PY - 2011

Y1 - 2011

N2 - The stability and activity of the low redox potential Melanocarpus albomyces laccase (MaL) in various aqueous organic (acetone, ethanol, propylene glycol, diethylene glycol monomethyl ether) solvent systems was studied spectrophotometrically using 2,6-dimethoxyphenol (2,6-DMP) as substrate. In addition, reactivity of the enzyme with two lignans; matairesinol (MR) and 7-hydroxymatairesinol (HMR), was examined by oxygen consumption measurements in the most potential aqueous organic solvent systems. Polymerization of the lignans by MaL was verified by matrix assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS) and size exclusion chromatography (SEC). Polymerization of the higher molecular weight lignin model compound, dehydrogenation polymers (DHPs), was studied by SEC. The solubilities of industrial softwood and hardwood kraft lignins were evaluated as parameters for investigation of enzymatic modification in aqueous organic solvent systems. The functioning of MaL in different aqueous organic media was excellent. Propylene glycol and diethylene glycol monomethyl ether were better solvents than ethanol or acetone in enzymatic oxidations. Even though they were the best solvents for enzyme oxidation, ethanol and propylene glycol were selected for further tests because of their different physicochemical properties. The results obtained in this study for the use of laccase-catalysed reactions in organic solvents to improve the efficiency of lignin oxidation may be exploited in several applications and areas in which the solubility of the reactants or products is a limiting factor.

AB - The stability and activity of the low redox potential Melanocarpus albomyces laccase (MaL) in various aqueous organic (acetone, ethanol, propylene glycol, diethylene glycol monomethyl ether) solvent systems was studied spectrophotometrically using 2,6-dimethoxyphenol (2,6-DMP) as substrate. In addition, reactivity of the enzyme with two lignans; matairesinol (MR) and 7-hydroxymatairesinol (HMR), was examined by oxygen consumption measurements in the most potential aqueous organic solvent systems. Polymerization of the lignans by MaL was verified by matrix assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS) and size exclusion chromatography (SEC). Polymerization of the higher molecular weight lignin model compound, dehydrogenation polymers (DHPs), was studied by SEC. The solubilities of industrial softwood and hardwood kraft lignins were evaluated as parameters for investigation of enzymatic modification in aqueous organic solvent systems. The functioning of MaL in different aqueous organic media was excellent. Propylene glycol and diethylene glycol monomethyl ether were better solvents than ethanol or acetone in enzymatic oxidations. Even though they were the best solvents for enzyme oxidation, ethanol and propylene glycol were selected for further tests because of their different physicochemical properties. The results obtained in this study for the use of laccase-catalysed reactions in organic solvents to improve the efficiency of lignin oxidation may be exploited in several applications and areas in which the solubility of the reactants or products is a limiting factor.

KW - Melanocarpus albomyces

KW - laccase

KW - solvent

KW - reactivity

KW - lignin

KW - lignans

KW - dehydrogenation polymers

U2 - 10.1016/j.molcatb.2011.05.009

DO - 10.1016/j.molcatb.2011.05.009

M3 - Article

VL - 72

SP - 122

EP - 129

JO - Journal of Molecular Catalysis B: Enzymatic

JF - Journal of Molecular Catalysis B: Enzymatic

SN - 1381-1177

IS - 3-4

ER -