Polymerization of Guaiacol and a Phenolic β‐O‐4‐Substructure by Trameteshirsuta Laccase in the Presence of ABTS

Klaus Rittstieg, Anna Suurnäkki, Tapani Suortti, Kristiina Kruus, Georg M. Guebitz (Corresponding Author), Johanna Buchert

Research output: Contribution to journalArticleScientificpeer-review

23 Citations (Scopus)

Abstract

The reaction of the monomeric lignin model compound guaiacol and the β‐O‐4‐type dimer erol (1–(4‐hydroxy‐3‐methoxyphenyl)–2(2‐methoxyphenoxy)‐propane‐1,3‐diol with laccase from Trametes hirsuta was studied in the presence of the mediator ABTS (2,2′‐azino‐di[3ethylbenzothiazoline‐6‐sulfonic acid]). The product mixtures were analyzed by means of aqueous‐phase size exclusion chromatography (SEC) with 50 mM NaOH as eluent. Interestingly, in the laccase‐catalyzed reaction with both substrates, the mediator not only functioned as an electron carrier but underwent coupling reactions with the substrate to give polymeric coupling products. The molecular weight of these copolymeric products was significantly higher than the molecular weight of products obtained without ABTS. After ultrafiltration, 33% and 21% of the initially applied ABTS could be found in the polymeric product fraction for the substrates guaiacol and erol, respectively, on the basis of nitrogen analysis. When ABTS was added to substrates after full laccase‐catalyzed polymerization, the reaction proceeded toward higher molecular weights.
Original languageEnglish
Pages (from-to)1505-1509
Number of pages5
JournalBiotechnology Progress
Volume19
Issue number5
DOIs
Publication statusPublished - 2003
MoE publication typeA1 Journal article-refereed

Fingerprint

Guaiacol
Laccase
Polymerization
Molecular Weight
Trametes
Lignin
Ultrafiltration
Gel Chromatography
Nitrogen
Electrons
Acids
2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid

Keywords

  • laccase
  • oxidases
  • Trametes hirsuta
  • guaiacol

Cite this

Rittstieg, Klaus ; Suurnäkki, Anna ; Suortti, Tapani ; Kruus, Kristiina ; Guebitz, Georg M. ; Buchert, Johanna. / Polymerization of Guaiacol and a Phenolic β‐O‐4‐Substructure by Trameteshirsuta Laccase in the Presence of ABTS. In: Biotechnology Progress. 2003 ; Vol. 19, No. 5. pp. 1505-1509.
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abstract = "The reaction of the monomeric lignin model compound guaiacol and the β‐O‐4‐type dimer erol (1–(4‐hydroxy‐3‐methoxyphenyl)–2(2‐methoxyphenoxy)‐propane‐1,3‐diol with laccase from Trametes hirsuta was studied in the presence of the mediator ABTS (2,2′‐azino‐di[3ethylbenzothiazoline‐6‐sulfonic acid]). The product mixtures were analyzed by means of aqueous‐phase size exclusion chromatography (SEC) with 50 mM NaOH as eluent. Interestingly, in the laccase‐catalyzed reaction with both substrates, the mediator not only functioned as an electron carrier but underwent coupling reactions with the substrate to give polymeric coupling products. The molecular weight of these copolymeric products was significantly higher than the molecular weight of products obtained without ABTS. After ultrafiltration, 33{\%} and 21{\%} of the initially applied ABTS could be found in the polymeric product fraction for the substrates guaiacol and erol, respectively, on the basis of nitrogen analysis. When ABTS was added to substrates after full laccase‐catalyzed polymerization, the reaction proceeded toward higher molecular weights.",
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Polymerization of Guaiacol and a Phenolic β‐O‐4‐Substructure by Trameteshirsuta Laccase in the Presence of ABTS. / Rittstieg, Klaus; Suurnäkki, Anna; Suortti, Tapani; Kruus, Kristiina; Guebitz, Georg M. (Corresponding Author); Buchert, Johanna.

In: Biotechnology Progress, Vol. 19, No. 5, 2003, p. 1505-1509.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Polymerization of Guaiacol and a Phenolic β‐O‐4‐Substructure by Trameteshirsuta Laccase in the Presence of ABTS

AU - Rittstieg, Klaus

AU - Suurnäkki, Anna

AU - Suortti, Tapani

AU - Kruus, Kristiina

AU - Guebitz, Georg M.

AU - Buchert, Johanna

PY - 2003

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N2 - The reaction of the monomeric lignin model compound guaiacol and the β‐O‐4‐type dimer erol (1–(4‐hydroxy‐3‐methoxyphenyl)–2(2‐methoxyphenoxy)‐propane‐1,3‐diol with laccase from Trametes hirsuta was studied in the presence of the mediator ABTS (2,2′‐azino‐di[3ethylbenzothiazoline‐6‐sulfonic acid]). The product mixtures were analyzed by means of aqueous‐phase size exclusion chromatography (SEC) with 50 mM NaOH as eluent. Interestingly, in the laccase‐catalyzed reaction with both substrates, the mediator not only functioned as an electron carrier but underwent coupling reactions with the substrate to give polymeric coupling products. The molecular weight of these copolymeric products was significantly higher than the molecular weight of products obtained without ABTS. After ultrafiltration, 33% and 21% of the initially applied ABTS could be found in the polymeric product fraction for the substrates guaiacol and erol, respectively, on the basis of nitrogen analysis. When ABTS was added to substrates after full laccase‐catalyzed polymerization, the reaction proceeded toward higher molecular weights.

AB - The reaction of the monomeric lignin model compound guaiacol and the β‐O‐4‐type dimer erol (1–(4‐hydroxy‐3‐methoxyphenyl)–2(2‐methoxyphenoxy)‐propane‐1,3‐diol with laccase from Trametes hirsuta was studied in the presence of the mediator ABTS (2,2′‐azino‐di[3ethylbenzothiazoline‐6‐sulfonic acid]). The product mixtures were analyzed by means of aqueous‐phase size exclusion chromatography (SEC) with 50 mM NaOH as eluent. Interestingly, in the laccase‐catalyzed reaction with both substrates, the mediator not only functioned as an electron carrier but underwent coupling reactions with the substrate to give polymeric coupling products. The molecular weight of these copolymeric products was significantly higher than the molecular weight of products obtained without ABTS. After ultrafiltration, 33% and 21% of the initially applied ABTS could be found in the polymeric product fraction for the substrates guaiacol and erol, respectively, on the basis of nitrogen analysis. When ABTS was added to substrates after full laccase‐catalyzed polymerization, the reaction proceeded toward higher molecular weights.

KW - laccase

KW - oxidases

KW - Trametes hirsuta

KW - guaiacol

U2 - 10.1021/bp034054z

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SP - 1505

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