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Alkyl-phenyl cleavage of the lignin model compounds guaiacylglycol and glycerol-β-guaiacyl ether by Phanerochaete chrysosporium

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Abstract

The white rot basidiomycete Phanerochaete chrysosporium metabolized guaiacylglycol-β-guaiacyl ether (I) in high nitrogen, shaking and stationary cultures. 2-(o-Methoxyphenoxy) ethanol (X), 2-(o-methoxyphenoxy) acetic acid (IX) and methoxy-phydroquinone (MHQ) were identified as products of the metabolism of (I). P. chrysosporium also metabolized guaiacylglycerol-β-guaiacyl ether (IV) in high nitrogen stationary cultures. 2-(o-Methoxyphenoxy)-1,3 propanediol (XII) and 3-hydroxy, 2-(o-methoxy-phenyxy) propionic acid (XIV) were identified as products of the metabolism of (IV). Finally, P. chrysosporium metabolized α-deoxyguaiacylglycol-β-guaiacyl ether (VI) and α-deoxyguaiacylglycerol-β-guaiacyl ether (VII) in limiting nitrogen cultures. 2-(o-Methoxyphenoxy) ethanol (X) and 2-(o-methoxyphenoxy)-1,3 propanediol (XII) were identified as products of the metabolism of VI and VII respectively indicating α hydroxylation of those substrates with subsequent alkyl-phenyl bond cleavage. Metabolites were identified after comparison with chemically synthesized standards by GLC-mass spectrometry.

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Abbreviations

GLC :

Gas liquid chromatography

TMSi :

trimethylsilyl

TLC :

thin layer chromatography

MHQ :

methoxyhydroquinone

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Goldsby, G.P., Enoki, A. & Gold, M.H. Alkyl-phenyl cleavage of the lignin model compounds guaiacylglycol and glycerol-β-guaiacyl ether by Phanerochaete chrysosporium . Arch. Microbiol. 128, 190–195 (1980). https://doi.org/10.1007/BF00406157

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