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Journal of Wood Science

Official Journal of the Japan Wood Research Society

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Investigation on hydrogen abstraction from methyl glucoside by active oxygen species under oxygen delignification conditions III: effects of the origin of active oxygen species

Journal of Wood Science volume 57, pages 512–519 (2011)Cite this article

Abstract

Carbohydrate model compounds methyl β-d-glucopyranoside (MGPβ), methyl α-d-glucopyranoside (MGPα), and methyl β-d-mannopyranoside (MMPβ) and the deuterium compounds of MGPβ labeled at the anomeric or C-2 positions (MGPβ-1D, MGPβ-2D) were reacted with active oxygen species (AOS) generated in situ by reactions between O2 and a co-treated phenolic lignin model compound, 4-hydroxy-3-methoxybenzyl alcohol (VAlc), under conditions simulating oxygen delignification (0.5 mol/l NaOH, 0.36 mmol/l Fe3+, 1.1 MPa O2, 95°C). MGPβ was degraded more than MGPα but less than MMPβ when the pairs MGPβ/MGPα and MGPβ/MMPβ, respectively, were treated, which indicates that the configurational differences at the anomeric and C-2 positions influence the reactivity of AOS toward these compounds. When the pairs MGPβ/MGPβ-1D and MGPβ/MGPβ-2D were treated, no clear kinetic isotope effects were observed in either case. These results contrasted with those obtained when another phenolic compound, 2,4,6-trimethylphenol (TMPh), was used as the AOS generator instead of VAlc under exactly the same conditions. Clear kinetic isotope effects were observed when using TMPh. Because it is not easily accepted that the anomeric and C-2 hydrogen abstractions are minor reaction modes only for AOS generated in the VAlc system, it is suspected that the AOS do not show any clear kinetic isotope effect even though the AOS abstract an objective hydrogen.

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Authors and Affiliations

  1. Laboratory of Wood Chemistry, Department of Biomaterial Sciences, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo, 113-8657, Japan

    Tomoya Yokoyama, Akihiko Nakagawa, Fumiko Konishi & Yuji Matsumoto

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  1. Tomoya Yokoyama
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  2. Akihiko Nakagawa
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  3. Fumiko Konishi
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  4. Yuji Matsumoto
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Correspondence to Tomoya Yokoyama.

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Yokoyama, T., Nakagawa, A., Konishi, F. et al. Investigation on hydrogen abstraction from methyl glucoside by active oxygen species under oxygen delignification conditions III: effects of the origin of active oxygen species. J Wood Sci 57, 512–519 (2011). https://doi.org/10.1007/s10086-011-1201-2

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  • DOI: https://doi.org/10.1007/s10086-011-1201-2

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