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Direct cleavage of the vicinal diol linkage of the lignin model compound dihydroanisoin by the basidiomycete Phanerochaete chrysosporium

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Abstract

The white rot basidiomycete Phanerochaete chrysosporium metabolized dihydroanisoin (1,2-dianisylethane-1,2 diol) in low nitrogen stationary cultures, conditions under which the ligninolytic system is expressed. Anisyl alcohol was isolated as a metabolic product indicating an initial diol bond cleavage of the substrate. Use of 3H-labeled dihydroanisoin (1,2-dianisylethane-1,2-diol-1,2 3H) indicated that the diol bond was cleaved directly, yielding anisyl aldehyde as the initial product. The metabolically stable ketol anisoin was shown not be an intermediate in the metabolism of dihydroanisoin. The diol cleavage reaction was dependent on the concentration of molecular oxygen but O2 could be replaced by H2O2 under some conditions. The cleavage reaction was inhibited by exogenously-added tyrosine2-Cu2+ complex (TCC). The appearance of the fungal diol cleavage system parallels the appearance of the ligninolytic system under a variety of physiological conditions. In addition, preincubation of ligninolytic cultures with 2.5 mM l-glutamate represses both the ligninolytic and the diol cleavage activities.

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Abbreviations

DHA:

Dihydroanisoin

GLC:

gas liquid chromatography

TLC:

thin layer chromatography

TMS:

trimethylsilyl

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  1. Mikio Shimada

    Present address: Wood Research Institute, Kyoto University, Uji, Kyoto, Japan

Authors and Affiliations

  1. Department of Chemistry and Biochemical Sciences, Oregon Graduate Center, 19600 N.W. Walker Road, 97006, Beaverton, Oregon, USA

    Mikio Shimada & Michael H. Gold

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  1. Mikio Shimada
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  2. Michael H. Gold
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Shimada, M., Gold, M.H. Direct cleavage of the vicinal diol linkage of the lignin model compound dihydroanisoin by the basidiomycete Phanerochaete chrysosporium . Arch. Microbiol. 134, 299–302 (1983). https://doi.org/10.1007/BF00407806

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  • DOI: https://doi.org/10.1007/BF00407806

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