Skip to main content
Log in

Stereospecific reduction of geraniol to (R)-(+)-citronellol bySaccharomyces cerevisiae

  • Specialia
  • Chimica, Biochimica
  • Published:
Experientia Aims and scope Submit manuscript

Summary

(R)-(+)-citronellol, a useful C10 chiral synthon for natural terpenoid products, can be obtained in enantiomerically pure form and satisfactory yield by yeast reduction of geraniol.

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

References

  1. C. Fuganti, D. Ghiringhelli and P. Grasselli, J. chem. Soc. chem. Commun.1975, 846;

  2. P. Gramatica, B. M. Ranzi and P. Manitto, Bioorg. Chem.10, 22 (1981).

    Article  CAS  Google Scholar 

  3. Natural (R)0-(+)-citronellal, from which (2) can be obtained, has been shown to be only 75–80% optically pure: H. E. Eschinazi, J. Org. Chem.26, 3072 (1961);

    Article  CAS  Google Scholar 

  4. G. W. O'Donnell and M. D. Sutherland, Aust. J. Chem.19, 525 (1966);

    Article  CAS  Google Scholar 

  5. F. Ciardelli and P. Pino, Ric. Sci. Rc. A4, 694 (1964); B. D. Sully and P. L. Williams, Perfum. essent. Oil Rec.59, 365 (1968).

    CAS  Google Scholar 

  6. 1×108 cell ml−1. The growth conditions ofSaccharomyces cerevisiae have been described in ref. 1b) G. W. O'Donnell and M. D. Sutherland, Aust. J. Chem.19, 525 (1966).

    Article  CAS  Google Scholar 

  7. Average of 6 independent experiments.

  8. C. G. Overberger and J. K. Weise, J. Am. chem. Soc.90, 3525 (1968);

    Article  CAS  Google Scholar 

  9. J. L. Simonsen, in: The terpenes, vol. 1, p. 28. Cambridge Press 1953;

  10. W. Karrer, in: Konstitution und Vorkommen der Organischen Pflanzenstoffe, p. 52. Eds H. Hürlimann and E. Cherbuliez. Birkhäuser, Basel 1958.

    Chapter  Google Scholar 

  11. R. Rienacker and G. Ohloff, Angew. Chem.77, 240 (1961).

    Article  Google Scholar 

  12. D. Valentine, K. K. Chan, C. G. Scott, K. K. Johnson, K. Toth and G. Saucy, J. org. Chem.41, 62 (1976).

    Article  CAS  Google Scholar 

  13. Compund (3) can be obtained from (2) by Ni-Raney hydrogenation without concomitant racemization9a.

  14. K. K. Chan, N. Cohen, J. P. DeNoble, A. C. Specian and G. Saucy, J. org. Chem.41, 3497 (1976);

    Article  CAS  PubMed  Google Scholar 

  15. N. Cohen, W. F. Eichel, R. J. Lopresti, C. Neukom and G. Saucy, J. org. Chem.41, 3505 (1976); C. Fuganti and P. Grasselli, J. chem. Soc. chem. Commun.1979, 995.

    Article  CAS  PubMed  Google Scholar 

  16. J. Kulesza, J. Gora, K. Kowalska, Z. Dogielska and M. Druri, Przem. chem.50 (9), 571 (1971); chem. Abstr.76, 14722t; T. P. Dang, P. Aviron-Violet, Y. Colleuille and J. Varagnat, 8th Congr. int. Huiles Essentielles, Cannes-Grasse 1980, abstract p. 158.

    CAS  Google Scholar 

  17. C. G. Overberger and H. Kaye, J. Am. chem. Soc.89, 5640 (1967).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gramatica, P., Manitto, P., Ranzi, B.M. et al. Stereospecific reduction of geraniol to (R)-(+)-citronellol bySaccharomyces cerevisiae. Experientia 38, 775–776 (1982). https://doi.org/10.1007/BF01972264

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01972264

Keywords

Navigation