Stereospecificity in enzymic and non‐enzymic oxidation of β‐O‐4 lignin model compounds

FEBS Letters

Lundquist, Knut¹  Jönsson, Leif²  Nyman, Per Olof²  Karlsson, Olov¹ 

[1] Department of Organic Chemistry, Chalmers University of Technology and University of Göteborg, S-412 96 Göteborg, Sweden;Division of Biochemistry, Chemical Center, University of Lund, PO Box 124, S-221 00 Lund, Sweden

关键词: Lignin model compound;    Stereospecificity;    Lignin peroxidase isozyme;    Trametes versicolor;    Cerium(IV) ammonium nitrate;    1H-NMR;    NMR;    nuclear magnetic resonance;    TLC;    thin-layer chromatography;    TMS;    tetramethylsilane;   

DOI  :  10.1016/0014-5793(90)80503-B

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

The degradation of the erythro and threo isomers of the non-phenolic lignin model compound 2-(2,6-dimethoxyphenoxy)-1-(3,4-dimethoxyphenyl)-1,3-propanediol was examined. Enzymic and non-enzymic oxidation of the diastereomers was performed with Trametes versicolor lignin peroxidase and cerium(IV) ammonium nitrate, respectively. Mixtures of approximately equal amounts of the diastereomers were partially degraded and subsequently analyzed with TLC and ¹H-NMR. Analysis of reaction mixtures from enzymic as well as non-enzymic oxidation, revealed a preferential degradation of the threo form. Preliminary analyses of enzymic reaction mixtures of either the erythro or threo isomer suggest they yield in part different products. The observations made would have implications for the understanding of how enzymes attack lignins. They should also be taken into consideration in experiments where model compounds are being used to mimic native lignin.

【 授权许可】

Unknown