Metabolism of 3-methyldiphenyl ether by Sphingomonas sp. SS31

FEMS Microbiol Lett. 1992 Sep 15;75(2-3):253-8. doi: 10.1016/0378-1097(92)90413-i.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adaptation, Physiological
  • Bacteria / metabolism*
  • Biodegradation, Environmental
  • Models, Chemical
  • Oxidation-Reduction
  • Oxygen Consumption
  • Phenyl Ethers / chemistry
  • Phenyl Ethers / metabolism*

Substances

  • Phenyl Ethers
  • 1-methyl-3-phenoxybenzene