The impact of lignin sulfonation on its reactivity with laccase and laccase/HBT

Roelant Hilgers, Megan Twentyman-Jones, Annemieke Van Dam, Harry Gruppen, Han Zuilhof, Mirjam A. Kabel, Jean Paul Vincken*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

1 Citation (Scopus)

Abstract

Lignin is a highly abundant aromatic polymer in nature, but its controlled cleavage or cross-linking is a major challenge and currently hindering industrial applicability. Laccase (L) and laccase/mediator systems (LMS) are promising tools for enzymatic lignin modification, but to date, their overall reaction outcome is hard to predict and control. This research aimed to understand the reactivity of native and sulfonated β-O-4 linked lignin structures in L and LMS treatments. Trametes versicolor laccase, and the mediator hydroxybenzotriazole (HBT) were used, and reaction products were analyzed using UHPLC-MS n and MALDI-TOF-MS. Polymerization was observed for both the native and sulfonated phenolic compounds, suggesting that sulfonation does not affect radical coupling of the phenolic lignin subunits. In contrast, sulfonation of the non-phenolic lignin structure prevented C α oxidation and cleavage by L/HBT, which was explained by an increased C α -H bond dissociation energy of ∼10 kcal mol -1 upon sulfonation. Overall, our results indicate that lignin sulfonation drives the overall outcome of LMS incubations towards polymerization.

Original languageEnglish
Pages (from-to)1535-1542
Number of pages8
JournalCatalysis Science and Technology
Volume9
Issue number6
DOIs
Publication statusPublished - 4 Mar 2019

Fingerprint

Laccase
Sulfonation
Lignin
Polymerization
Aromatic polymers
Reaction products
Oxidation

Cite this

@article{7e29a7760013410ca63dc86fce75d4c3,
title = "The impact of lignin sulfonation on its reactivity with laccase and laccase/HBT",
abstract = "Lignin is a highly abundant aromatic polymer in nature, but its controlled cleavage or cross-linking is a major challenge and currently hindering industrial applicability. Laccase (L) and laccase/mediator systems (LMS) are promising tools for enzymatic lignin modification, but to date, their overall reaction outcome is hard to predict and control. This research aimed to understand the reactivity of native and sulfonated β-O-4 linked lignin structures in L and LMS treatments. Trametes versicolor laccase, and the mediator hydroxybenzotriazole (HBT) were used, and reaction products were analyzed using UHPLC-MS n and MALDI-TOF-MS. Polymerization was observed for both the native and sulfonated phenolic compounds, suggesting that sulfonation does not affect radical coupling of the phenolic lignin subunits. In contrast, sulfonation of the non-phenolic lignin structure prevented C α oxidation and cleavage by L/HBT, which was explained by an increased C α -H bond dissociation energy of ∼10 kcal mol -1 upon sulfonation. Overall, our results indicate that lignin sulfonation drives the overall outcome of LMS incubations towards polymerization.",
author = "Roelant Hilgers and Megan Twentyman-Jones and {Van Dam}, Annemieke and Harry Gruppen and Han Zuilhof and Kabel, {Mirjam A.} and Vincken, {Jean Paul}",
year = "2019",
month = "3",
day = "4",
doi = "10.1039/c9cy00249a",
language = "English",
volume = "9",
pages = "1535--1542",
journal = "Catalysis Science & Technology",
issn = "2044-4753",
publisher = "Royal Society of Chemistry",
number = "6",

}

The impact of lignin sulfonation on its reactivity with laccase and laccase/HBT. / Hilgers, Roelant; Twentyman-Jones, Megan; Van Dam, Annemieke; Gruppen, Harry; Zuilhof, Han; Kabel, Mirjam A.; Vincken, Jean Paul.

In: Catalysis Science and Technology, Vol. 9, No. 6, 04.03.2019, p. 1535-1542.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - The impact of lignin sulfonation on its reactivity with laccase and laccase/HBT

AU - Hilgers, Roelant

AU - Twentyman-Jones, Megan

AU - Van Dam, Annemieke

AU - Gruppen, Harry

AU - Zuilhof, Han

AU - Kabel, Mirjam A.

AU - Vincken, Jean Paul

PY - 2019/3/4

Y1 - 2019/3/4

N2 - Lignin is a highly abundant aromatic polymer in nature, but its controlled cleavage or cross-linking is a major challenge and currently hindering industrial applicability. Laccase (L) and laccase/mediator systems (LMS) are promising tools for enzymatic lignin modification, but to date, their overall reaction outcome is hard to predict and control. This research aimed to understand the reactivity of native and sulfonated β-O-4 linked lignin structures in L and LMS treatments. Trametes versicolor laccase, and the mediator hydroxybenzotriazole (HBT) were used, and reaction products were analyzed using UHPLC-MS n and MALDI-TOF-MS. Polymerization was observed for both the native and sulfonated phenolic compounds, suggesting that sulfonation does not affect radical coupling of the phenolic lignin subunits. In contrast, sulfonation of the non-phenolic lignin structure prevented C α oxidation and cleavage by L/HBT, which was explained by an increased C α -H bond dissociation energy of ∼10 kcal mol -1 upon sulfonation. Overall, our results indicate that lignin sulfonation drives the overall outcome of LMS incubations towards polymerization.

AB - Lignin is a highly abundant aromatic polymer in nature, but its controlled cleavage or cross-linking is a major challenge and currently hindering industrial applicability. Laccase (L) and laccase/mediator systems (LMS) are promising tools for enzymatic lignin modification, but to date, their overall reaction outcome is hard to predict and control. This research aimed to understand the reactivity of native and sulfonated β-O-4 linked lignin structures in L and LMS treatments. Trametes versicolor laccase, and the mediator hydroxybenzotriazole (HBT) were used, and reaction products were analyzed using UHPLC-MS n and MALDI-TOF-MS. Polymerization was observed for both the native and sulfonated phenolic compounds, suggesting that sulfonation does not affect radical coupling of the phenolic lignin subunits. In contrast, sulfonation of the non-phenolic lignin structure prevented C α oxidation and cleavage by L/HBT, which was explained by an increased C α -H bond dissociation energy of ∼10 kcal mol -1 upon sulfonation. Overall, our results indicate that lignin sulfonation drives the overall outcome of LMS incubations towards polymerization.

U2 - 10.1039/c9cy00249a

DO - 10.1039/c9cy00249a

M3 - Article

VL - 9

SP - 1535

EP - 1542

JO - Catalysis Science & Technology

JF - Catalysis Science & Technology

SN - 2044-4753

IS - 6

ER -