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Depolymerization of Laccase-Oxidized Lignin in Aqueous Alkaline Solution at 37 °C

  • Haifeng Liu
    Haifeng Liu
    Institute of Biotechnology, RWTH Aachen University, Worringerweg 3, 52074 Aachen, Germany
    More by Haifeng Liu
  • Leilei Zhu
    Leilei Zhu
    Institute of Biotechnology, RWTH Aachen University, Worringerweg 3, 52074 Aachen, Germany
    Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, 300308 Tianjin, China
    More by Leilei Zhu
  • Anne-Maria Wallraf
    Anne-Maria Wallraf
    Institute of Biotechnology, RWTH Aachen University, Worringerweg 3, 52074 Aachen, Germany
  • Christoph Räuber
    Christoph Räuber
    Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52056 Aachen, Germany
  • Philipp M. Grande
    Philipp M. Grande
    Institut für Technische und Makromolekulare Chemie (ITMC), RWTH Aachen University, Worringerweg 1, 52074 Aachen, Germany
  • Nico Anders
    Nico Anders
    Aachener Verfahrenstechnik−Enzyme Process Technology, RWTH Aachen University, Worringerweg 1, 52074 Aachen, Germany
    More by Nico Anders
  • Christoph Gertler
    Christoph Gertler
    Institute of Biotechnology, RWTH Aachen University, Worringerweg 3, 52074 Aachen, Germany
  • Bernd Werner
    Bernd Werner
    Institute of Chemistry, University of Graz, Heinrichstraße 28/II, 8010 Graz, Austria
    More by Bernd Werner
  • Jürgen Klankermayer
    Jürgen Klankermayer
    Institut für Technische und Makromolekulare Chemie (ITMC), RWTH Aachen University, Worringerweg 1, 52074 Aachen, Germany
  • Walter Leitner
    Walter Leitner
    Institut für Technische und Makromolekulare Chemie (ITMC), RWTH Aachen University, Worringerweg 1, 52074 Aachen, Germany
    Max Planck Institute for Chemical Energy Conversion, Stiftstraße 34-36, 45470 Mülheim a.d. Ruhr, Germany
  • , and 
  • Ulrich Schwaneberg*
    Ulrich Schwaneberg
    Institute of Biotechnology, RWTH Aachen University, Worringerweg 3, 52074 Aachen, Germany
    DWI an der RWTH Aachen e.V., Forckenbeckstraße 50, 52056 Aachen, Germany
    *E-mail: [email protected] (U.S.).
Cite this: ACS Sustainable Chem. Eng. 2019, 7, 13, 11150–11156
Publication Date (Web):June 3, 2019
https://doi.org/10.1021/acssuschemeng.9b00204
Copyright © 2019 American Chemical Society

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    Abstract

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    Lignin depolymerization is a coveted process for the generation of high-value compounds from a low-cost feedstock. This report describes a chemoenzymatic approach for the depolymerization of lignin involving a laccase-catalyzed oxidation under ambient air at room temperature followed by a base (NaOH)-induced depolymerization in aqueous solution at 37 °C. Two-dimensional nuclear magnetic resonance heteronuclear single quantum coherence spectroscopy, gel permeation chromatography, and liquid chromatography-electrospray ionization-quadrupole-time of flight-mass spectrometry (LC-ESI-Q-TOF-MS) analysis indicated the degradation of lignin and the formation of water-soluble fractions containing guaiacol, syringol, vanillic acid, m-anisic acid, and veratric acid. Furthermore, guaiacol and veratric acid are the main final products in the chemoenzymatic decomposition of a β-O-4 model compound.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acssuschemeng.9b00204.

    • Spectroscopic data of the isolated products; characterization of the OrganoCat lignin samples, β-O-4 model compound, DDQ oxidized OrganoCat lignin based on HSQC spectra; GPC measurements for the OrganoCat lignin samples; LC-MS and HPLC measurements for the OrganoCat lignin samples (PDF)

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    Cited By

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    2. Luyao Wang, Liping Tan, Liqiu Hu, Xiaoju Wang, Rajesh Koppolu, Teija Tirri, Bas van Bochove, Petri Ihalainen, Liji Sobhana Seleenmary Sobhanadhas, Jukka V. Seppälä, Stefan Willför, Martti Toivakka, Chunlin Xu. On Laccase-Catalyzed Polymerization of Biorefinery Lignin Fractions and Alignment of Lignin Nanoparticles on the Nanocellulose Surface via One-Pot Water-Phase Synthesis. ACS Sustainable Chemistry & Engineering 2021, 9 (26) , 8770-8782. https://doi.org/10.1021/acssuschemeng.1c01576
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    13. Zichen Wang, Mingtian Hao, Xiaoyu Li, Beibei Zhang, Mingyang Jiao, Bo-Zhen Chen. Promising and efficient lignin degradation versatile strategy based on DFT calculations. iScience 2022, 25 (2) , 103755. https://doi.org/10.1016/j.isci.2022.103755
    14. Toshiyuki Itoh, Yumiko Takagi. Activation and stabilization of enzymes using ionic liquid engineering. 2022, 57-83. https://doi.org/10.1016/B978-0-323-91306-5.00014-5
    15. Avnish Kumar, Bijoy Biswas, Ramandeep Kaur, Bhavya B Krishna, Thallada Bhaskar. Hydrothermal oxidative valorisation of lignin into functional chemicals: A review. Bioresource Technology 2021, 342 , 126016. https://doi.org/10.1016/j.biortech.2021.126016
    16. Xiu-Zhi Wei, Jianguo Liu, Longlong Ma. Cleavage via Selective Catalytic Oxidation of Lignin or Lignin Model Compounds into Functional Chemicals. ChemEngineering 2021, 5 (4) , 74. https://doi.org/10.3390/chemengineering5040074
    17. Weiran Zhang, Weiwei Wang, Jinghong Wang, Guinan Shen, Yuan Yuan, Lei Yan, Hongzhi Tang, Weidong Wang, . Isolation and Characterization of a Novel Laccase for Lignin Degradation, LacZ1. Applied and Environmental Microbiology 2021, 87 (23) https://doi.org/10.1128/AEM.01355-21
    18. Dachang Bai, Junyan Chen, Bingbing Zheng, Xueyan Li, Junbiao Chang. Catalytic [3+3] Annulation of β‐Ketoethers and Cyclopropenones via C(sp 3 )—O/C—C Bond Cleavage under Transition‐Metal Free Conditions. Chinese Journal of Chemistry 2021, 39 (10) , 2769-2773. https://doi.org/10.1002/cjoc.202100276
    19. P. Sivagurunathan, Tirath Raj, Chandra Sekhar Mohanta, Surbhi Semwal, Alok Satlewal, Ravi P. Gupta, Suresh K. Puri, S.S.V. Ramakumar, Ravindra Kumar. 2G waste lignin to fuel and high value-added chemicals: Approaches, challenges and future outlook for sustainable development. Chemosphere 2021, 268 , 129326. https://doi.org/10.1016/j.chemosphere.2020.129326
    20. Sandip K. Singh. Biological treatment of plant biomass and factors affecting bioactivity. Journal of Cleaner Production 2021, 279 , 123546. https://doi.org/10.1016/j.jclepro.2020.123546
    21. Nico Anders, Maike van Ohlen, Tim Jestel, Laura Herbst, Mohamed Amine Jmel, Issam Smaali, Antje C. Spiess. Uncover aldehydes in biomass hydrolyzates: disproportionation of aldehydes in alkaline solution and subsequent measurement using an automated HPAEC-PAD method. Analytical and Bioanalytical Chemistry 2020, 412 (23) , 5593-5600. https://doi.org/10.1007/s00216-020-02775-6
    22. Chen Sun, Lei Zheng, Wenhao Xu, Alexandr V. Dushkin, Weike Su. Mechanochemical cleavage of lignin models and lignin via oxidation and a subsequent base-catalyzed strategy. Green Chemistry 2020, 22 (11) , 3489-3494. https://doi.org/10.1039/D0GC00372G
    23. Longcheng Hong, Astrid Spielmeyer, Janin Pfeiffer, Hermann A. Wegner. Domino lignin depolymerization and reconnection to complex molecules mediated by boryl radicals. Catalysis Science & Technology 2020, 10 (9) , 3008-3014. https://doi.org/10.1039/D0CY00558D
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