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.

  • Letter
  • Published:

Formation of 2-Iminothiazolidine-4-carboxylic Acid in the Cyanobromination of Lanthionine

Abstract

Sullivan and Folk1 found that the symmetrical thioether, lanthionine, is converted quantitatively into cysteine by the combined action of cyanogen bromide and sodium cyanide. Although we could confirm the presence of cysteine in the reaction products we were unable to substantiate the quantitative nature of this conversion. The heterocyclic compound 2-iminothiazolidine-4-carboxylic acid, which we detected in the mixture after reaction, could have been formed by further reaction of cysteine on the cyanogen halide and could account for our low cysteine yields.

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

Access options

Buy this article

USD 39.95

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

Similar content being viewed by others

References

  1. Sullivan, M. X., and Folk, J. E., Arch. Biochem., Biophys., 35, 305 (1952).

    Article  CAS  Google Scholar 

  2. Sullivan, M. X., U.S. Pub. Health Dept., Suppl. No. 78 (1929).

  3. Zahn, H., and Traumann, K., Melliand Textilber., 35, 1069 (1954).

    CAS  Google Scholar 

  4. Nakamura, K., and Binkley, F., J. Biol. Chem., 173, 407 (1948).

    CAS  PubMed  Google Scholar 

  5. Aldridge, W., Biochem. J., 48, 271 (1951).

    Article  CAS  Google Scholar 

  6. Dann, J. R., Oliver, G. L., and Gates, J. W., J. Amer. Chem. Soc., 79, 1644 (1957).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

VAN RENSBURG, N. Formation of 2-Iminothiazolidine-4-carboxylic Acid in the Cyanobromination of Lanthionine. Nature 200, 672–673 (1963). https://doi.org/10.1038/200672b0

Download citation

  • Issue date:

  • DOI: https://doi.org/10.1038/200672b0

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