New degradation compounds from lignocellulosic biomass pretreatment: routes for formation of potent oligophenolic enzyme inhibitors

H. Rasmussen, David Ackland Tanner, H. R. Sørensen, Anne S. Meyer

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Abstract

In this study 26 new oligophenol cellulase inhibitors were discovered from wheat straw pretreatment liquors. By consideration of the reaction mechanisms for their formation it is proposed that these oligophenols are formed during hydrothermal biomass pretreatment by pentose self-condensation reactions involving aldol condensations, 1,4 additions to α,β unsaturated carbonyl compounds, 3-keto acid decarboxylations and oxidations. Furthermore, pentose reactions with phenolic lignin components are suggested. The identification of the central role of xylose in the reaction routes for oligophenolic inhibitor formation led to the solution to protect the reactive anomeric center in xylose. It is shown that protection of the anomeric center in in situ generated xylose with ethylene glycol monobutyl ether, during pretreatment of wheat straw, reduces the level of oligophenols by 73%. The results pave the way for implementation of new types of reactions that hinder inhibitor formation in lignocellulosic biomass processing.
Original languageEnglish
JournalGreen Chemistry
Volume19
Pages (from-to)464-473
Number of pages10
ISSN1463-9262
DOIs
Publication statusPublished - 2017

Bibliographical note

This article is published Open Access as part of the RSC's Gold for Gold initiative, licensed under a Creative Commons Attribution 3.0 Unported Licence.

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