Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • News & Views
  • Published:

Supramolecular catalysis

Terpenes in tight spaces

The ability of enzymes to direct the synthesis of complex natural products from simple starting materials is epitomized by terpene biosynthesis. Now, a supramolecular catalyst has been shown to mimic some of the reactivity of this process.

This is a preview of subscription content, access via your institution

Relevant articles

Open Access articles citing this article.

Access options

Buy this article

Prices may be subject to local taxes which are calculated during checkout

Figure 1: Non-stop polycyclization/rearrangement controlled by terpene cyclase enzymes.
Figure 2: Supramolecular tail-to-head cyclization.

References

  1. Robinson, R. J. Chem. Soc. Trans. 111, 876–899 (1917).

    Article  CAS  Google Scholar 

  2. Woodward, R. B. & Bloch, K. J. Am. Chem. Soc. 75, 2023–2024 (1953).

    Article  CAS  Google Scholar 

  3. Eschenmoser, A., Ruzicka, L., Jeger, O. & Arigoni, D. Helv. Chim. Acta 38, 1890–1904 (1955).

    Article  CAS  Google Scholar 

  4. Stork, G. & Burgstahler, A. W. J. Am. Chem. Soc. 77, 5068–5077 (1955).

    Article  CAS  Google Scholar 

  5. Kohler, R. E. Model Studies for the Synthesis of β-Amyrin PhD thesis, Harvard Univ. (1965).

    Google Scholar 

  6. Meischer, K. & Wieland, P. Helv. Chim. Acta. 33, 1847–1864 (1950).

    Article  Google Scholar 

  7. Wendt, K. U., Schulz, G. E., Corey, E. J. & Liu, D. R. Angew. Chem. Int. Ed. 39, 2812–2833 (2000).

    Article  CAS  Google Scholar 

  8. Christianson, D. W. Chem. Rev. 106, 3412–3442 (2006).

    Article  CAS  Google Scholar 

  9. Zhang, Q. & Tiefenbacher, K. Nature Chem. 7, 197–202 (2015).

    Article  CAS  Google Scholar 

  10. Breslow, R. & Dong, S. D. Chem. Rev. 98, 1997–2011 (1998).

    Article  CAS  Google Scholar 

  11. Hof, F., Craig, S. L., Nuckolls, C. & Rebek, J. Jr. Angew. Chem. Int. Ed. 41, 1488–1508 (2002).

    Article  CAS  Google Scholar 

  12. Zhao, C., Toste, F. D., Raymond, K. N. & Bergman, R. G. J. Am. Chem. Soc. 136, 14409–14412 (2014).

    Article  CAS  Google Scholar 

  13. Hart-Cooper, W. M., Clary, K. N., Toste, F. D., Bergman, R. G. & Raymond, K. N. J. Am. Chem. Soc. 134, 17873–17876 (2012).

    Article  CAS  Google Scholar 

  14. Pluth, M. D., Bergman, R. G. & Raymond, K. N. J. Am. Chem. Soc. 129, 11459–11467 (2007).

    Article  CAS  Google Scholar 

  15. Pronin, S. V. & Shenvi, R. A. Nature Chem. 4, 915–920 (2012).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ryan A. Shenvi.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Roach, J., Shenvi, R. Terpenes in tight spaces. Nature Chem 7, 187–189 (2015). https://doi.org/10.1038/nchem.2191

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/nchem.2191

This article is cited by

Search

Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing