Oxidation of carbazole to 3-hydroxycarbazole by naphthalene 1,2-dioxygenase and biphenyl 2,3-dioxygenase

FEMS Microbiol Lett. 1993 Nov 1;113(3):297-302. doi: 10.1111/j.1574-6968.1993.tb06530.x.

Abstract

Naphthalene 1,2-dioxygenase from Pseudomonas sp. NCIB 9816-4 and biphenyl dioxygenase from Beijerinckia sp. B8/36 oxidized the aromatic N-heterocycle carbazole to 3-hydroxycarbazole. Toluene dioxygenase from Pseudomonas putida F39/D did not oxidize carbazole. Transformations were carried out by mutant strains which oxidize naphthalene and biphenyl to cis-dihydrodiols, and with a recombinant E. coli strain expressing the structural genes of naphthalene 1,2-dioxgenase from Pseudomonas sp. NCIB 9816-4. 3-Hydroxycarbazole is presumed to result from the dehydration of an unstable cis-dihydrodiol.

Publication types

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

MeSH terms

  • Bacteria / enzymology*
  • Bacteria / metabolism
  • Carbazoles / metabolism*
  • Dioxygenases
  • Iron-Sulfur Proteins*
  • Multienzyme Complexes / metabolism*
  • Oxidation-Reduction
  • Oxygenases / metabolism*

Substances

  • Carbazoles
  • Iron-Sulfur Proteins
  • Multienzyme Complexes
  • carbazole
  • 3-hydroxycarbazole
  • Oxygenases
  • Dioxygenases
  • naphthalene dioxygenase
  • biphenyl-2,3-dioxygenase