Nativity of lignin carbohydrate bonds substantiated by biomimetic synthesis

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Volume Title

A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä

Date

2019-10-24

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Language

en

Pages

11
5591-5601

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JOURNAL OF EXPERIMENTAL BOTANY, Volume 70, issue 20

Abstract

The question of whether lignin is covalently linked to carbohydrates in native wood, forming what is referred to as lignin-carbohydrate complexes (LCCs), still lacks unequivocal proof. This is mainly due to the need to isolate lignin from woody materials prior to analysis, under conditions leading to partial chemical modification of the native wood polymers. Thus, the correlation between the structure of the isolated LCCs and LCCs in situ remains open. As a way to circumvent the problematic isolation, biomimicking lignin polymerization in vivo and in vitro is an interesting option. Herein, we report the detection of lignin-carbohydrate bonds in the extracellular lignin formed by tissue-cultured Norway spruce cells, and in modified biomimetic lignin synthesis (dehydrogenation polymers). Semi-quantitative 2D heteronuclear singular quantum coherence (HSQC)-, 31P -, and 13C-NMR spectroscopy were applied as analytical tools. Combining results from these systems, four types of lignin-carbohydrate bonds were detected; benzyl ether, benzyl ester, γ-ester, and phenyl glycoside linkages, providing direct evidence of lignin-carbohydrate bond formation in biomimicked lignin polymerization. Based on our findings, we propose a sequence for lignin-carbohydrate bond formation in plant cell walls.

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Keywords

Benzyl ester, benzyl ether, dehydrogenation polymer, gamma (γ)-ester, lignin-carbohydrate complex, phenyl glycoside, xtracellular lignin

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Citation

Giummarella, N, Balakshin, M, Koutaniemi, S, Kärkönen, A, Lawoko, M & Zhao, Q 2019, ' Nativity of lignin carbohydrate bonds substantiated by biomimetic synthesis ', Journal of Experimental Botany, vol. 70, no. 20, pp. 5591-5601 . https://doi.org/10.1093/jxb/erz324