On the reactions of two fungal laccases differing in their redox potential with lignin model compounds: Products and their rate of formation

Maarit Lahtinen (Corresponding Author), Kristiina Kruus, Petri Heinonen, Jussi Sipilä

Research output: Contribution to journalArticleScientificpeer-review

33 Citations (Scopus)

Abstract

Laccases (EC 1.10.3.2) are multicopper oxidases able to oxidize phenolic compounds such as lignin-related polyphenols. Since the discovery that so-called mediators effectively extend the family of laccase substrates, direct interactions between lignin-like materials and laccase have gained much less attention. In this work, the aim was to characterize oxidation products formed in direct laccase-catalyzed oxidation of different guaiacylic and syringylic lignin model compounds with two different laccases: a low redox potential Melanocarpus albomyces laccase and a high redox potential Trametes hirsuta laccase. By following the formation of different, mainly biphenylic (5-5) and benzylic oxidation products, it was found that although both of these enzymes generated practically the same pattern of products with particular types of syringyl and guaiacyl compounds, in some cases a clear difference in the rates of their formation was observed. The results also confirm further to the suggestions that syringylic compounds are able to act as mediators in their own oxidation reactions and also that in some instances acetylation of phenolic material may produce altered, unexpected structures.
Original languageEnglish
Pages (from-to)8357-8365
Number of pages9
JournalJournal of Agricultural and Food Chemistry
Volume57
Issue number18
DOIs
Publication statusPublished - 2009
MoE publication typeA1 Journal article-refereed

Fingerprint

Laccase
laccase
Lignin
redox potential
Oxidation-Reduction
lignin
Oxidation
oxidation
Trametes
Coriolus hirsutus
Acetylation
Polyphenols
acetylation
Oxidoreductases
phenolic compounds
polyphenols
Substrates
Enzymes
enzymes

Keywords

  • Laccase
  • lignin
  • model compound
  • guaiacyl
  • syringyl
  • oxidation
  • product structure
  • nuclear magnetic resonance spectroscopy
  • liquid chromatography - mass spectrometry
  • electrospray ionizationb mass spectrometry
  • redox potential
  • Trametes hirsuta
  • Melanocarpus albomyces

Cite this

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title = "On the reactions of two fungal laccases differing in their redox potential with lignin model compounds: Products and their rate of formation",
abstract = "Laccases (EC 1.10.3.2) are multicopper oxidases able to oxidize phenolic compounds such as lignin-related polyphenols. Since the discovery that so-called mediators effectively extend the family of laccase substrates, direct interactions between lignin-like materials and laccase have gained much less attention. In this work, the aim was to characterize oxidation products formed in direct laccase-catalyzed oxidation of different guaiacylic and syringylic lignin model compounds with two different laccases: a low redox potential Melanocarpus albomyces laccase and a high redox potential Trametes hirsuta laccase. By following the formation of different, mainly biphenylic (5-5) and benzylic oxidation products, it was found that although both of these enzymes generated practically the same pattern of products with particular types of syringyl and guaiacyl compounds, in some cases a clear difference in the rates of their formation was observed. The results also confirm further to the suggestions that syringylic compounds are able to act as mediators in their own oxidation reactions and also that in some instances acetylation of phenolic material may produce altered, unexpected structures.",
keywords = "Laccase, lignin, model compound, guaiacyl, syringyl, oxidation, product structure, nuclear magnetic resonance spectroscopy, liquid chromatography - mass spectrometry, electrospray ionizationb mass spectrometry, redox potential, Trametes hirsuta, Melanocarpus albomyces",
author = "Maarit Lahtinen and Kristiina Kruus and Petri Heinonen and Jussi Sipil{\"a}",
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On the reactions of two fungal laccases differing in their redox potential with lignin model compounds : Products and their rate of formation. / Lahtinen, Maarit (Corresponding Author); Kruus, Kristiina; Heinonen, Petri; Sipilä, Jussi.

In: Journal of Agricultural and Food Chemistry, Vol. 57, No. 18, 2009, p. 8357-8365.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - On the reactions of two fungal laccases differing in their redox potential with lignin model compounds

T2 - Products and their rate of formation

AU - Lahtinen, Maarit

AU - Kruus, Kristiina

AU - Heinonen, Petri

AU - Sipilä, Jussi

PY - 2009

Y1 - 2009

N2 - Laccases (EC 1.10.3.2) are multicopper oxidases able to oxidize phenolic compounds such as lignin-related polyphenols. Since the discovery that so-called mediators effectively extend the family of laccase substrates, direct interactions between lignin-like materials and laccase have gained much less attention. In this work, the aim was to characterize oxidation products formed in direct laccase-catalyzed oxidation of different guaiacylic and syringylic lignin model compounds with two different laccases: a low redox potential Melanocarpus albomyces laccase and a high redox potential Trametes hirsuta laccase. By following the formation of different, mainly biphenylic (5-5) and benzylic oxidation products, it was found that although both of these enzymes generated practically the same pattern of products with particular types of syringyl and guaiacyl compounds, in some cases a clear difference in the rates of their formation was observed. The results also confirm further to the suggestions that syringylic compounds are able to act as mediators in their own oxidation reactions and also that in some instances acetylation of phenolic material may produce altered, unexpected structures.

AB - Laccases (EC 1.10.3.2) are multicopper oxidases able to oxidize phenolic compounds such as lignin-related polyphenols. Since the discovery that so-called mediators effectively extend the family of laccase substrates, direct interactions between lignin-like materials and laccase have gained much less attention. In this work, the aim was to characterize oxidation products formed in direct laccase-catalyzed oxidation of different guaiacylic and syringylic lignin model compounds with two different laccases: a low redox potential Melanocarpus albomyces laccase and a high redox potential Trametes hirsuta laccase. By following the formation of different, mainly biphenylic (5-5) and benzylic oxidation products, it was found that although both of these enzymes generated practically the same pattern of products with particular types of syringyl and guaiacyl compounds, in some cases a clear difference in the rates of their formation was observed. The results also confirm further to the suggestions that syringylic compounds are able to act as mediators in their own oxidation reactions and also that in some instances acetylation of phenolic material may produce altered, unexpected structures.

KW - Laccase

KW - lignin

KW - model compound

KW - guaiacyl

KW - syringyl

KW - oxidation

KW - product structure

KW - nuclear magnetic resonance spectroscopy

KW - liquid chromatography - mass spectrometry

KW - electrospray ionizationb mass spectrometry

KW - redox potential

KW - Trametes hirsuta

KW - Melanocarpus albomyces

U2 - 10.1021/jf901511k

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M3 - Article

VL - 57

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EP - 8365

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

SN - 0021-8561

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