Metabolism of 3-methyldiphenyl ether by Sphingomonas sp. SS31.
The bacterium Sphingomonas sp. SS31, which was obtained from the diphenyl ether-degrading strain Sphingomonas sp. SS3 by an adaptation process, utilized 3-methyldiphenyl ether for growth in addition to diphenyl ether. The initial enzymatic attack onto this compound proceeded by a regioselective, but non-specific dioxygenation at the carbon carrying the ether bridge and the adjacent carbon of the unsubstituted as well as the methyl-substituted aromatic nucleus. Upon spontaneous decomposition, the resulting unstable hemiacetal structure yielded 3-methylphenol and catechol, or phenol, 3-methylcatechol, and 4-methylcatechol, respectively. Phenol and 3-methylphenol were oxidized to the corresponding catechols which, after subsequent ortho-cleavage, were channeled into the oxoadipate pathway.
Schmidt
S
S
Institut für Allgemeine Botanik, Abteilung für Mikrobiologie, Universität Hamburg, FRG.
Wittich
R M
RM
Fortnagel
P
P
Erdmann
D
D
Francke
W
W
D000222:Adaptation, Physiological; D001419:Bacteria / Q000378:metabolism*; D001673:Biodegradation, Environmental; D008956:Models, Chemical; D010084:Oxidation-Reduction; D010101:Oxygen Consumption; D010647:Phenyl Ethers / Q000737:chemistry / Q000378:metabolism*
D010647:Phenyl Ethers; C077432:1-methyl-3-phenoxybenzene