Journal of Industrial Microbiology

, Volume 17, Issue 5, pp 438–457

Diverse reactions catalyzed by naphthalene dioxygenase fromPseudomonas sp strain NCIB 9816

  • SM Resnick
  • K Lee
  • DT Gibson
Article

DOI: 10.1007/BF01574775

Cite this article as:
Resnick, S., Lee, K. & Gibson, D. Journal of Industrial Microbiology & Biotechnology (1996) 17: 438. doi:10.1007/BF01574775

Abstract

Naphthalene dioxygenase (NDO) fromPseudomonas sp strain NCIB 9816 is a multicomponent enzyme system which initiates naphthalene catabolism by catalyzing the addition of both atoms of molecular oxygen and two hydrogen atoms to the substrate to yield enantiomerically pure (+)-cis-(1R,2S)-dihydroxy-1,2-dihydronaphthalene. NDO has a relaxed substrate specificity and catalyzes the dioxygenation of many related 2- and 3-ring aromatic and hydroaromatic (benzocyclic) compounds to their respectivecis-diols. Biotransformations with a diol-accumulating mutant, recombinant strains and purified enzyme components have established that in addition tocis-dihydroxylation, NDO also catalyzes a variety of other oxidations which include monohydroxylation, desaturation (dehydrogenation),O-andN-dealkylation and sulfoxidation reactions. In several cases, the absolute stereochemistry of the oxidation products formed by NDO are opposite to those formed by toluene dioxygenase (TDO). The reactions catalyzed by NDO and other microbial dioxygenases can yield specific hydroxylated compounds which can serve as chiral synthons in the preparation of a variety of compounds of interest to pharmaceutical and specialty chemical industries. We present here recent work documenting the diverse array of oxidation reactions catalyzed by NDO. The trends observed in the oxidation of a series of benzocyclic aromatic compounds are compared to those observed with TDO and provide the basis for prediction of regio- and stereospecificity in the oxidation of related substrates. Based on the types of reactions catalyzed and the biochemical characteristics of NDO, a mechanism for oxygen activation by NDO is proposed.

Keywords

asymmetric dihydroxylation biocatalysis biotransformation dealkylation desaturation dioxygenation monooxygenation sulfoxidation stereospecific oxidation 

Copyright information

© Society for Industrial Microbiology 1996

Authors and Affiliations

  • SM Resnick
    • 1
    • 2
  • K Lee
    • 1
    • 2
  • DT Gibson
    • 1
    • 2
  1. 1.The Department of MicrobiologyThe University of IowaIowa CityUSA
  2. 2.The Center for Biocatalysis and BioprocessingThe University of IowaIowa CityUSA

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