OXIDATIVE METABOLISM OF PHENANTHRENE AND ANTHRACENE BY SOIL PSEUDOMONADS. THE RING-FISSION MECHANISM

Biochem J. 1965 Jun;95(3):819-31. doi: 10.1042/bj0950819.

Abstract

1. Phenanthrene is oxidatively metabolized by soil pseudomonads through trans-3,4-dihydro-3,4-dihydroxyphenanthrene to 3,4-dihydroxyphenanthrene, which then undergoes cleavage. 2. Some properties of the ring-fission product, cis-4-(1-hydroxynaphth-2-yl)-2-oxobut-3-enoic acid, are described. The Fe(2+)-dependent oxygenase therefore disrupts the bond between C-4 and the angular C of the phenanthrene nucleus. 3. An enzyme of the aldolase type converts the fission product into 1-hydroxy-2-naphthaldehyde (2-formyl-1-hydroxynaphthalene). An NAD-specific dehydrogenase is also present in the cell-free extract, which oxidizes the aldehyde to 1-hydroxy-2-naphthoic acid. This is then oxidatively decarboxylated to 1,2-dihydroxynaphthalene, thus allowing continuation of metabolism via the naphthalene pathway. 4. Anthracene is similarly metabolized, through 1,2-dihydro-1,2-dihydroxyanthracene to 1,2-dihydroxyanthracene, in which ring-fission occurs to give cis-4-(2-hydroxynaphth-3-yl)-2-oxobut-3-enoic acid. The position of cleavage is again at the bond between the angular C and C-1 of the anthracene nucleus. 5. Enzymes that convert the fission product through 2-hydroxy-3-naphthaldehyde into 2-hydroxy-3-naphthoic acid were demonstrated. The further metabolism of this acid is discussed. 6. The Fe(2+)-dependent oxygenase responsible for cleavage of all the o-dihydroxyphenol derivatives appears to be catechol 2,3-oxygenase, and is a constitutive enzyme in the Pseudomonas strains used.

MeSH terms

  • Aldehydes*
  • Anthracenes*
  • Chromatography*
  • Coumarins*
  • Infrared Rays*
  • Metabolism*
  • Naphthalenes*
  • Naphthols*
  • Phenanthrenes*
  • Pseudomonas aeruginosa*
  • Pseudomonas*
  • Research*
  • Soil Microbiology*
  • Soil*

Substances

  • 1-hydroxy-2-naphthaldehyde
  • 2-hydroxy-3-naphthoic acid
  • Aldehydes
  • Anthracenes
  • Coumarins
  • Naphthalenes
  • Naphthols
  • Phenanthrenes
  • Soil
  • naphthalene
  • 1-naphthol
  • 1,2-dihydroxynaphthalene
  • phenanthrene
  • 2-naphthaldehyde
  • anthracene
  • 2-naphthol
  • 1-hydroxy-2-naphthoic acid