Synthesis and enzymatic hydrolysis of a diaryl benzyl ester model of a lignin-carbohydrate complex (LCC)
Journal article, 2016

Specific degradation of the bonds between lignin and carbohydrates is an important step towards separating individual lignocellulosic biopolymers for sustainable production of materials and chemicals. One of the most established covalent lignin-carbohydrate (LC) interactions is the ester bond between the α-or γ-hydroxyl group of a lignin phenylpropane unit and a glucuronic acid side chain of xylan. In this work, a model of the LC benzyl ester bond was synthesized in a one-pot reaction from a β-O-4 lignin unit and d-glucuronic acid, both from commercial sources. The resulting lignin-carbohydrate complex (LCC) model was unstable in aqueous solution. However, at pH 4, the rate of spontaneous hydrolysis was sufficiently low to allow for enzymatic splitting experiments. The enzymatic hydrolysis of the LC benzyl ester bond of the LCC model was demonstrated by means of the glucuronoyl esterase StGE2 from Sporotrichum thermophile, which showed a preference for erythro forms of the LCC model.

quinone methide

glucuronoyl esterase

CE15

lignin-carbohydrate complex

D-glucuronic acid

StGE2

Author

Filip Nylander

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Organic Chemistry

Hampus Sunner

Chalmers, Biology and Biological Engineering, Industrial Biotechnology

Paul Christakopoulos

Wallenberg Wood Science Center (WWSC)

Lisbeth Olsson

Wallenberg Wood Science Center (WWSC)

Chalmers, Biology and Biological Engineering, Industrial Biotechnology

Gunnar Westman

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Organic Chemistry

Wallenberg Wood Science Center (WWSC)

Holzforschung

0018-3830 (ISSN) 1437-434X (eISSN)

Vol. 70 5 385-391

Areas of Advance

Energy

Subject Categories

Other Chemical Engineering

Biocatalysis and Enzyme Technology

DOI

10.1515/hf2014-0347

More information

Latest update

8/15/2018