Polymerization of coniferyl alcohol by Mn3+-mediated (enzymatic) oxidation: Effects of H2O2 concentration, aqueous organic solvents, and pH

Roberto Taboada-Puig (Corresponding Author), Thelmo Lú-Chau, María Moreira, Gumersindo Feijoo, Juan Lema, Kurt Fagerstedt, Taina Ohra-aho, Tiina Liitiä, Harri Heikkinen, Jarmo Ropponen, Tarja Tamminen

    Research output: Contribution to journalArticleScientificpeer-review

    1 Citation (Scopus)

    Abstract

    The objective of this study was to evaluate the ability of one versatile peroxidase and the biocatalytically generated complex Mn(III)-malonate to polymerize coniferyl alcohol (CA) to obtain dehydrogenation polymers (DHPs) and to characterize how closely the structures of the formed DHPs resemble native lignin. Hydrogen peroxide was used as oxidant and Mn2+ as mediator. Based on the yields of the polymerized product, it was concluded that the enzymatic reaction should be performed in aqueous solution without organic solvents at 4.5 ≤ pH ≤ 6.0 and with 0.75 ≤ H2O2:CA ratio ≤ 1. The results obtained from the Mn3+-malonate-mediated polymerization showed that the yield was almost 100%. Reaction conditions had, however, effect on the structures of the formed DHPs, as detected by size exclusion chromatography and pyrolysis-GC/MS. It can be concluded that from the structural point of view, the optimal pH for DHP formation using the presently studied system was 3 or 4.5. Low H2O2/CA ratio was beneficial to avoid oxidative side reactions. However, the high frequency of β–β linkages in all cases points to dimer formation between monomeric CA rather than endwise polymerization.
    Original languageEnglish
    Pages (from-to)81-90
    Number of pages10
    JournalBiotechnology Progress
    Volume34
    Issue number1
    Early online date10 Oct 2017
    DOIs
    Publication statusPublished - 2018
    MoE publication typeNot Eligible

    Keywords

    • bjerkandera sp
    • coniferyl alcohol
    • dehydrogenated polymer
    • Mn(III)-malonate
    • polymerization
    • versatile peroxidase

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