Desaturation, dioxygenation, and monooxygenation reactions catalyzed by naphthalene dioxygenase from Pseudomonas sp. strain 9816-4

J Bacteriol. 1995 May;177(10):2615-21. doi: 10.1128/jb.177.10.2615-2621.1995.


The stereospecific oxidation of indan and indene was examined with mutant and recombinant strains expressing naphthalene dioxygenase of Pseudomonas sp. strain 9816-4. Pseudomonas sp. strain 9816/11 and Escherichia coli JM109(DE3)[pDTG141] oxidized indan to (+)-(1S)-indanol, (+)-cis-(1R,2S)-indandiol, (+)-(1S)-indenol, and 1-indanone. The same strains oxidized indene to (+)-cis-(1R,2S)-indandiol and (+)-(1S)-indenol. Purified naphthalene dioxygenase oxidized indan to the same four products formed by strains 9816/11 and JM109(DE3)[pDTG141]. In addition, indene was identified as an intermediate in indan oxidation. The major products formed from indene by purified naphthalene dioxygenase were (+)-(1S)-indenol and (+)-(1R,2S)-indandiol. The results show that naphthalene dioxygenase catalyzes the enantiospecific monooxygenation of indan to (+)-(1S)-indanol and the desaturation of indan to indene, which then serves as a substrate for the formation of (+)-(1R,2S)-indandiol and (+)-(1S)-indenol. The relationship of the desaturase, monooxygenase, and dioxygenase activities of naphthalene dioxygenase is discussed with reference to reactions catalyzed by toluene dioxygenase, plant desaturases, cytochrome P-450, methane monooxygenase, and other bacterial monooxygenases.

Publication types

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

MeSH terms

  • Benzofurans / metabolism
  • Biodegradation, Environmental
  • Dioxygenases
  • Electron Transport
  • Hydroxylation
  • Indans / metabolism*
  • Indenes / metabolism*
  • Indoles / metabolism
  • Multienzyme Complexes / genetics
  • Multienzyme Complexes / metabolism*
  • Oxygenases / genetics
  • Oxygenases / metabolism*
  • Pseudomonas / enzymology*
  • Recombinant Proteins / metabolism
  • Stereoisomerism
  • Substrate Specificity


  • Benzofurans
  • Indans
  • Indenes
  • Indoles
  • Multienzyme Complexes
  • Recombinant Proteins
  • 1,2-indanediol
  • 1-indenol
  • 1-indanol
  • indene
  • indoline
  • coumaran
  • Oxygenases
  • Dioxygenases
  • naphthalene dioxygenase
  • indan