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

Org Biomol Chem. 2016 Jul 12;14(28):6826-32. 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.

MeSH terms

  • Acrylonitrile / chemical synthesis
  • Acrylonitrile / chemistry
  • Copper / chemistry
  • Homoserine / chemical synthesis
  • Homoserine / chemistry
  • Indigofera / chemistry*
  • Lactones / chemical synthesis
  • Lactones / chemistry
  • Norleucine / analogs & derivatives*
  • Norleucine / chemical synthesis
  • Norleucine / chemistry
  • Zinc / chemistry

Substances

  • Lactones
  • Homoserine
  • Copper
  • Norleucine
  • Zinc
  • Acrylonitrile
  • indospicine