title: Synthesis of l-indospicine, [5,5,6-(2)H3]-l-indospicine and l-norindospicine.
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.
authors.affiliation: School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane 4072, Australia. j.devoss@uq.edu.au.
authors.forename: Cheng-Shan
authors.initials: CS
authors.lastname: Lang
authors.affiliation: School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane 4072, Australia. j.devoss@uq.edu.au.
authors.forename: Siew-Hoon
authors.initials: SH
authors.lastname: Wong
authors.affiliation: School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane 4072, Australia. j.devoss@uq.edu.au.
authors.forename: Sharon
authors.initials: S
authors.lastname: Chow
authors.affiliation: School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane 4072, Australia. j.devoss@uq.edu.au.
authors.forename: Victoria L
authors.initials: VL
authors.lastname: Challinor
authors.affiliation: Queensland Alliance for Agriculture and Food Innovation (QAAFI), The University of Queensland, Health and Food Sciences Precinct, Cooper Plains, QLD 4108, Australia.
authors.forename: Ken W L
authors.initials: KW
authors.lastname: Yong
authors.affiliation: Queensland Alliance for Agriculture and Food Innovation (QAAFI), The University of Queensland, Health and Food Sciences Precinct, Cooper Plains, QLD 4108, Australia.
authors.forename: Mary T
authors.initials: MT
authors.lastname: Fletcher
authors.affiliation: National Research Centre for Environmental and Toxicology, The University of Queensland, Health and Food Sciences Precinct, Cooper Plains, QLD 4108, Australia.
authors.forename: Dionne M
authors.initials: DM
authors.lastname: Arthur
authors.affiliation: National Research Centre for Environmental and Toxicology, The University of Queensland, Health and Food Sciences Precinct, Cooper Plains, QLD 4108, Australia.
authors.forename: Jack C
authors.initials: JC
authors.lastname: Ng
authors.affiliation: School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane 4072, Australia. j.devoss@uq.edu.au.
authors.forename: James J
authors.initials: JJ
authors.lastname: De Voss
mesh_terms: D000181:Acrylonitrile / Q000138:chemical synthesis / Q000737:chemistry; D003300:Copper / Q000737:chemistry; D006714:Homoserine / Q000138:chemical synthesis / Q000737:chemistry; D029883:Indigofera / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D009646:Norleucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015032:Zinc / Q000737:chemistry
chemical_list: D007783:Lactones; D006714:Homoserine; D003300:Copper; D009646:Norleucine; D015032:Zinc; D000181:Acrylonitrile; C058318:indospicine