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

Organic & Biomolecular Chemistry Pub Date: 2016-06-20 DOI: 10.1039/C6OB01187J

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
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