Novel ring cleavage products in the biotransformation of biphenyl by the yeast Trichosporon mucoides.
The yeast Trichosporon mucoides, grown on either glucose or phenol, was able to transform biphenyl into a variety of mono-, di-, and trihydroxylated derivatives hydroxylated on one or both aromatic rings. While some of these products accumulated in the supernatant as dead end products, the ortho-substituted dihydroxylated biphenyls were substrates for further oxidation and ring fission. These ring fission products were identified by high-performance liquid chromatography, gas chromatography-mass spectrometry, and nuclear magnetic resonance analyses as phenyl derivatives of hydroxymuconic acids and the corresponding pyrones. Seven novel products out of eight resulted from the oxidation and ring fission of 3,4-dihydroxybiphenyl. Using this compound as a substrate, 2-hydroxy-4-phenylmuconic acid, (5-oxo-3-phenyl-2,5-dihydrofuran-2-yl)acetic acid, and 3-phenyl-2-pyrone-6-carboxylic acid were identified. Ring cleavage of 3,4,4'-trihydroxybiphenyl resulted in the formation of [5-oxo-3-(4'-hydroxyphenyl)-2,5-dihydrofuran-2-yl]acetic acid, 4-(4'-hydroxyphenyl)-2-pyrone-6-carboxylic acid, and 3-(4'-hydroxyphenyl)-2-pyrone-6-carboxylic acid. 2,3,4-trihydroxybiphenyl was oxidized to 2-hydroxy-5-phenylmuconic acid, and 4-phenyl-2-pyrone-6-carboxylic acid was the transformation product of 3,4,5-trihydroxybiphenyl. All these ring fission products were considerably less toxic than the hydroxylated derivatives.
Sietmann
R
R
Institut für Mikrobiologie und Molekularbiologie, Ernst-Moritz-Arndt-Universität, D-17487 Greifswald, Germany. sietmann@biologie.uni-greifwald.de
Hammer
E
E
Specht
M
M
Cerniglia
C E
CE
Schauer
F
F
D001673:Biodegradation, Environmental; D001713:Biphenyl Compounds / Q000737:chemistry / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D003470:Culture Media; D008401:Gas Chromatography-Mass Spectrometry; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D014250:Trichosporon / Q000254:growth & development / Q000378:metabolism*
D001713:Biphenyl Compounds; D003470:Culture Media; C010574:biphenyl