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Oligomerization of Syringic Acid, a Lignin Derivative, by a Phenoloxidase¹

ABSTRACT

Syringic acid, a phenolic derivative from lignin, could be polymerized by a iaccase from the fungus Rhizoctonia praticola, and various oligomers ranging from dimers to hexamers were determined. Seven different dimers could be established by mass-spectrometric analysis, and each dimer yielded oligomers with corresponding molecular characteristics. The molecular structure of two dimers and one trimer, as well as their methylated or reductively acetylated derivatives, were identified by high-resolution mass and nuclear magnetic resonance (NMR) spectroscopy. Syringic acid was also converted to 2,6-dimethoxybenzoquinone, and this monomer could not be further oxidized by the fungal enzyme.

¹ Contribution from the Laboratory of Soil Microbiology, Dep. of Agron, and Dep. of Chem., The Pennsylvania State Univ., University Park, PA 16802. Journal Series no. 6,227 of the Pennsylvania Agric. Exp. Stn.

² Research Aide, Lecturer in Chemistry, and Professor of Soil Microbiology, respectively.

Received for publication May 11, 1981. Accepted for publication July 16, 1981.