Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 28, 2016
Previous Article Next Article

Synthesis of l-indospicine, [5,5,6-2H3]-l-indospicine and l-norindospicine

Author affiliations

Abstract

Indospicine is a non-proteogenic amino acid that accumulates as the free amino acid in livestock grazing Indigofera plant species and causes both reproductive losses and hepatotoxic effects. An efficient synthetic route to L-indospicine from L-homoserine lactone is described. The methodology is applicable for the synthesis of both deuterium labelled isotopomers and structural analogues for utilisation in biological studies. The key steps are a zinc mediated Barbier reaction with acrylonitrile and a Pinner reaction that together introduce the target amidine moiety.

Graphical abstract: Synthesis of l-indospicine, [5,5,6-2H3]-l-indospicine and l-norindospicine

Back to tab navigation

Supplementary files

Article information


Submitted
01 Jun 2016
Accepted
20 Jun 2016
First published
20 Jun 2016

Org. Biomol. Chem., 2016,14, 6826-6832
Article type
Paper

Synthesis of L-indospicine, [5,5,6-2H3]-L-indospicine and L-norindospicine

C. Lang, S. Wong, S. Chow, V. L. Challinor, K. W. L. Yong, M. T. Fletcher, D. M. Arthur, J. C. Ng and J. J. De Voss, Org. Biomol. Chem., 2016, 14, 6826
DOI: 10.1039/C6OB01187J

Social activity

Search articles by author

Spotlight

Advertisements