Phthalate pathway of phenanthrene metabolism: formation of 2'-carboxybenzalpyruvate

J Bacteriol. 1983 Apr;154(1):113-7. doi: 10.1128/jb.154.1.113-117.1983.

Abstract

The metabolism of phenanthrene by a gram-negative organism able to use this compound as a sole source of carbon and energy has been examined. 1-Hydroxy-2-naphthoic acid was oxidized by oxygen in a reaction catalyzed by a dioxygenase which was activated by ferrous ions. The stoichiometry of the oxidation and the UV spectrum of the product were consistent with the identification of the product as 2'-carboxybenzalpyruvate. This was confirmed by cleaving the product with a partially purified aldolase to yield 2-carboxybenzaldehyde and pyruvate. A number of enzymes for the metabolism of 1-hydroxy-2-naphthoic acid were induced by growth on phthalate or (less well) by growth on protocatechuate. The latter supported only a slow rate of growth, and this and poor induction may have been due to a slow rate of entry into the cell.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Gram-Negative Aerobic Bacteria / metabolism*
  • Phenanthrenes / metabolism*
  • Phenylpyruvic Acids / metabolism*
  • Phthalic Acids / metabolism*

Substances

  • Phenanthrenes
  • Phenylpyruvic Acids
  • Phthalic Acids
  • phenanthrene
  • phthalic acid
  • 2'-carboxybenzalpyruvate