1887

Abstract

sp. strain RWM1 grew with (-)-menthol, (-)-menthone and other acyclic monoterpenes as sole carbon sources. Growth on menthol was very slow, with a doubling time of more than 24 h, and was not rapid with (-)-menthone (doubling time 12 h). Concentrations of either carbon source greater than 0.025% inhibited growth. (-)-Menthone-grown cultures transiently accumulated 3,7-dimethyl-6-hydroxyoctanoate during growth, and (-)-menthol-grown cells oxidized (-)-menthol, (-)-menthone, 3,7-dimethyl-6-octanolide and 3,7-dimethyl-6-hydroxyoctanoate. Although neither a menthol oxidase nor a menthol dehydrogenase could be detected in extracts of (-)-menthol- or (-)-menthone-grown cells, an induced NADPH-linked monooxygenase with activity towards (-)-menthone was readily detected. With crude cell extracts, only 3,7-dimethyl-6-hydroxyoctanoate was detected as the reaction product. When the (-)-menthone monooxygenase was separated from an induced 3,7-dimethyl-6-octanolide hydrolase by chromatography on hydroxyapatite, the lactone 3,7-dimethyl-6-octanolide was shown to be the product of oxygenation.

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1994-03-01
2021-04-21
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References

  1. Baeyer A., Villiger V. 1899; Einwerkkung des caro’schen reagens auf ketone. Ber Dtsch Chem Ges 32:3625–3633
    [Google Scholar]
  2. Bennett A. P., Strang E. J., Trudgill P. W., Wong V. T. K. 1988; Purification and properties of e-caprolactone hydrolases from Acinetobacter NCIB 9871 and Nocardia globerula CL1. J Gen Microbiol 134:161–168
    [Google Scholar]
  3. Brougham P., Cooper M. S., Cummerson D. A., Heaney H., Thompson N. 1987; Oxidation reactions using magnesium monoperphthalate: a comparison with w-chloroperoxybenzoic acid. Synthesis 11:1015–1017
    [Google Scholar]
  4. Cain R. B. 1961; The metabolism of protocatechuic acid by a Vibrio . Biochem J 79:298–312
    [Google Scholar]
  5. Cantwell S.G., Lau E. P., Watts D. S., Fall R. R. 1978; Biodégradation of acyclic isoprenoids by Pseudomonas species. J Bacteriol 135:324–333
    [Google Scholar]
  6. Conrad H. E., Dubus R., Namtvedt M. J., Gunsalus I. C. 1965; Mixed function oxidation. II. Separation and properties of the enzymes catalysing camphor lactonization. J Biol Chem 240:495–503
    [Google Scholar]
  7. Donoghue N. A., Norris D. B., Trudgill P. W. 1976; The purification and properties of cyclohexanone oxygenase from Nocardia globerula CL1 and Acinetobacter NCIB 8971. Eur J Biochem 63:175–192
    [Google Scholar]
  8. Griffin M., Trudgill P. W. 1972; The metabolism of cyclo- pentanol by Pseudomonas NCIB 9872. Biochem J 129:595–603
    [Google Scholar]
  9. Griffiths E. T., Bociek S. M., Harries P. C., Jeffcoat R., Sissons D. J., Trudgill P. W. 1987a; Bacterial metabolism of a-μlnene: pathway from a-μlnene oxide to acyclic metabolites in Nocardia sp. strain μl8.3. J Bacteriol 169:4972–4979
    [Google Scholar]
  10. Griffiths E. T., Harries P. C., Jeffcoat R., Trudgill P. W. 1987b; Purification and properties of a-μlnene oxide lyase from Nocardia sp. strain μl8.3. J Bacteriol 169:4980–4983
    [Google Scholar]
  11. Gornall A. G., Bardawill C. J., David M. M. 1949; Determination of serum proteins by means of the biuret reaction. J Biol Chem 111:751–766
    [Google Scholar]
  12. Gunsalus I. C., Marshall V. P. 1971; Monoterpene dissimilation: chemical and genetic models. CRC Crit Ren Microbiol 1:291–310
    [Google Scholar]
  13. Krisch K. 1971; Carboxyesterase hydrolases. In The Enzymes vol 5 pp 43–69 Edited by Boyer P. D. New York: Academic Press;
    [Google Scholar]
  14. Mejbaum-Katzenellenbogen W., Dobryszycka W. M. 1959; New method for quantitative determination of serum proteins separated by paper electrophoresis. Clin Chim Acta 4:515–522
    [Google Scholar]
  15. Nakajima O., Iriye R., Hayashi T. 1976; Conversion of ( −)- menthone by Pseudomonas putida strain YK-2. Nippon Nagei Kagaku Kaishi 50:403–408
    [Google Scholar]
  16. Nakajima O., Iriye R., Hayashi T. 1978; Conversion of ( −)- menthone by Pseudomonas putida strain YK-2: metabolic intermediate and stereochemical structure of the metabolic products. Nippon Nagei Kagaku Kaishi 52:167–174
    [Google Scholar]
  17. Ougham H. J., Taylor D. G., Trudgill P. W. 1983; Camphor revisited: involvement of a unique monooxygenase in the metabolism of 2-oxo-A3-4,5,5-trimethylcyclopentenylacetic acid by Pseudomonas putida . J Bacteriol 153:140–152
    [Google Scholar]
  18. Rosenberger R. F., Elsden S. R. 1960; The yields of Streptococcus faecalis grown in continuous culture. J Gen Microbiol 22:726–739
    [Google Scholar]
  19. Sawamura N., Shima S., Sakai H. 1976; Conversion of ( −)- menthone by Pseudomonas fluorescens M-2. Agric Biol Chem 40:649–653
    [Google Scholar]
  20. Seubert W., Fass E., Remberger U. 1963; Untersuchungen über den bakteriellen abbau von isoprenoiden III. Reinigung und eigenschaften der geranylcarboxylase. Biochem Z 338:265–275
    [Google Scholar]
  21. Shukla O. P., Bartholomus R. C., Gunsalus I. C. 1987; Microbial transformation of menthol and menthan-3,4-diol. Can J Microbiol 33:489–497
    [Google Scholar]
  22. Simonsen J. L. 1947 The Terpenes, 2nd edn. vol 1 Cambridge: Cambridge University Press;
    [Google Scholar]
  23. Trudgill P. W. 1984; Microbial degradation of the alicyclic ring. In Microbial Degradation of Organic Compounds pp 131–180 Edited by Gibson D. T. New York: Marcel Dekker;
    [Google Scholar]
  24. Williams D. R., Trudgill P. W., Taylor D. G. 1989; Metabolism of 1,8-cineole by a Rhodococcus species: ring cleavage reactions. J Gen Microbiol 135:1957–1967
    [Google Scholar]
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