Skip to main content
Log in

Bioconversion of aniline to acetaminophen and overproduction of acetaminophen byStreptomyces spp.

  • Original Articles
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

In order to obtain acetaminophen, a popular analgesic-antipyretic, though microbial p-hydroxylation and N-acetylation of aniline, variousStreptomyces strains were screened. Aniline N-acetylation activity was rather ubiquitous but p-hydroxylation activity was selective. Microbial conversion pathway of aniline to acetaminophen was considered to be through N-acetylation and p-hydroxylation orvice versa. However, depending on species used, o-hydroxylation and its degradation activity (S. fradiae) and acetaminophen degradation activity (S. coelicolar) were also detected. Among the screenedStreptomyces strains.S. fradiae NRRL 2702 showed the highest acetanilide p-hydroxylation activity (2–3% conversion rate). Furthermore, inS. fradiae carbon source and its concentration, phosphate ion concentration and pH of growth medium were found to play the crucial roles in p-hydroxylation activity. Through the proper combination of factors mentioned above, the ten times more activity (26–30% conversion rate) was attained.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature Cited

  1. Gibson, D. T.: Microbial degradation of aromatic compounds.Science 161, 1093 (1968).

    Article  CAS  Google Scholar 

  2. Ferris, J. P., Fasco, M. J., Stylianopoulou, F. L., Jerina, D. M., Daily, J. W. and Jeffrey, A. M.: Monooxygenase activity inCunninghamella bainieri: Evidence for a fungal system similar to liver microsomes.Arch. Biochem. Biophys. 156, 97 (1973).

    Article  PubMed  CAS  Google Scholar 

  3. Berg, A. and Rafter, J.: Studies on the substrate specificity and inducibility of cytochrome P-450meg.Biochem. J.,196, 781 (1981).

    PubMed  CAS  Google Scholar 

  4. Smith, R. V. and Rosazza, J. P.: Microbial models of mammalian metabolism. Aromatic hydroxylation.Arch. Biochem. Biophys. 161, 551 (1974).

    Article  PubMed  CAS  Google Scholar 

  5. Sohn, Y. W. and Lee, S. S.: Microbial synthesis of acetaminophen.Seoul Univ. J. Pharm. Sci. 12 (1987).

  6. Theriault, R. J. and Longfield: Microbial conversion of acetanilide to 2-hydroxyacetanilide and 4-hydroxyacetanilide.Appl. Microbiol. 67, 1431 (1967).

    Google Scholar 

  7. Demain, A. L.: Catabolic regulation in industrial microbiology inOverproduction of microbial products. FEMS symposium ed. Krumphanzl, V., Sikyta, B. and Banek, Z., Academic Press Inc., New York, pp. 3 (1982).

    Google Scholar 

  8. Fulco, A. J.: P450BM-3 and other inducible bacterial P450 cytochromes: Biochemistry and regulation.Ann. Rev. Pharmacol. Toxicol. 31, 177 (1991).

    Article  CAS  Google Scholar 

  9. Okey, A. B.: Enzyme induction in the cytochrome P-450 system.Pharmacol. Ther. 45, 241 (1990).

    Article  PubMed  CAS  Google Scholar 

  10. Sariaslani, F. S. and Kunz, D. A.: Induction of cytochrome P-450 inStreptomyces griseus soybean flour.Biochem. Biopophys. Res. Commun. 141, 405 (1986).

    Article  CAS  Google Scholar 

  11. Fulco, A. J. and Ruettinger, R. T.: Occurrence of a barbiturate-inductible catalytically self-sufficient 119,000 dalton cytochrome P-450 monooxygenase inBacilli.Life Sic. 40, 1769 (1987).

    Article  CAS  Google Scholar 

  12. Hathway, D. E.: Plant phenols and tannins. InChromatographic and electrophoretic techniques. vol. 1 ed. Smith, I., Wm. Heinemann Medical Book Ltd., London, p. 324 (1960).

    Google Scholar 

  13. Shihabi, Z. K. and David, R. M.: Colorimetric assay for acetaminophen in serum.Ther. Drug Monitor. 6, 449 (1984).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Jin, H.J., Park, A.K. & Lee, S.S. Bioconversion of aniline to acetaminophen and overproduction of acetaminophen byStreptomyces spp.. Arch. Pharm. Res. 15, 41–47 (1992). https://doi.org/10.1007/BF02973982

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02973982

Keywords

Navigation