Applied Microbiology and Biotechnology

, Volume 56, Issue 3–4, pp 453–457

Biological production of optically active muconolactones by Rhodococcus rhodochrous

  •  C.-J. Cha
Original Paper

DOI: 10.1007/s002530100668

Cite this article as:
Cha, CJ. Appl Microbiol Biotechnol (2001) 56: 453. doi:10.1007/s002530100668


Optically active (-)-3-methylmuconolactone was biologically produced using a mutant strain of Rhodococcus rhodochrous N75 that is capable of metabolizing 4-methylcatechol via a modified ortho-cleavage pathway. The mutant strain (CJ30) was prepared by mutagenesis using N-methyl-N'-nitro-N-nitrosoguanidine and found to be blocked in the degradation of 3-methylmuconolactone. Cells of the mutant CJ30, which had been previously grown on yeast extract and induced with p-toluate, transformed p-toluate (11.5 mM) to optically active (-)-3-methylmuconolactone with a yield of 53%. The structure of 3-methylmuconolactone was confirmed by NMR spectroscopy and mass spectrometry. Cell-free extracts of R. rhodochrous N75 also transformed a range of 4-alkylcatechols, such as 4-ethylcatechol, 4-iso-propylcatechol, and 4-tert-butylcatechol, to the corresponding 4-alkyl-substituted muconolactones.

Copyright information

© Springer-Verlag 2001

Authors and Affiliations

  •  C.-J. Cha
    • 1
  1. 1.Institute of Biotechnology, University of Cambridge, Tennis Court Road, Cambridge CB2 1QT, UK
  2. 2.Present address: Division of Microbiology, National Center for Toxicological Research, U. S. Food and Drug Administration, 3900 NCTR Road, Jefferson, AR 72079, USA

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