Degradation of 2-hydroxybiphenyl and 2,2'-dihydroxybiphenyl by Pseudomonas sp. strain HBP1

Appl Environ Microbiol. 1988 Nov;54(11):2683-8. doi: 10.1128/aem.54.11.2683-2688.1988.

Abstract

Pseudomonas sp. strain HBP1 was found to grow on 2-hydroxy- and 2,2'-dihydroxy-biphenyl as the sole carbon and energy sources. The first step in the degradation of these compounds was catalyzed by an NADH-dependent monooxygenase. The enzyme inserted a hydroxyl group adjacent to the already existing hydroxyl group to form 2,3-dihydroxybiphenyl when acting on 2-hydroxybiphenyl and to form 2,2',3-trihydroxybiphenyl when acting on 2,2'-dihydroxybiphenyl. To be substrates of the monooxygenase, compounds required a 2-hydroxyphenyl-R structure, with R being a hydrophobic group (e.g., methyl, ethyl, propyl, sec-butyl, phenyl, or 2-hydroxyphenyl). Several chlorinated hydroxybiphenyls served as pseudosubstrates by effecting consumption of NADH and oxygen without being hydroxylated. Further degradation of 2,3-dihydroxy- and 2,2',3-trihydroxybiphenyl involved meta cleavage, with subsequent formation of benzoate and salicylate, respectively.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Biodegradation, Environmental
  • Biphenyl Compounds / metabolism*
  • Chemical Phenomena
  • Chemistry
  • Hydrogen-Ion Concentration
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Mixed Function Oxygenases / metabolism*
  • Oxygen / metabolism
  • Phenols / metabolism*
  • Pseudomonas / enzymology
  • Pseudomonas / growth & development
  • Pseudomonas / metabolism*
  • Sewage
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet

Substances

  • Biphenyl Compounds
  • Phenols
  • Sewage
  • 2-phenylphenol
  • Mixed Function Oxygenases
  • 2-hydroxybiphenyl 3-monooxygenase
  • 2,2'-biphenol
  • Oxygen