Synthesis of L-Indospicine, [5,5,6-2H3 ]- L-Indospicine and L-Norindospicine

Lang, Cheng-Shan, Wong, Siew-Hoon, Chow, Sharon, Challinor, Victoria L., Yong, Ken W. L., Fletcher, Mary T., Arthur, Dionne M., Ng, Jack C. and De Voss, James J. (2016) Synthesis of L-Indospicine, [5,5,6-2H3 ]- L-Indospicine and L-Norindospicine. Organic and Biomolecular Chemistry, 14 28: 6826-6832. doi:10.1039/C6OB01187J


Author Lang, Cheng-Shan
Wong, Siew-Hoon
Chow, Sharon
Challinor, Victoria L.
Yong, Ken W. L.
Fletcher, Mary T.
Arthur, Dionne M.
Ng, Jack C.
De Voss, James J.
Title Synthesis of L-Indospicine, [5,5,6-2H3 ]- L-Indospicine and L-Norindospicine
Formatted title
Synthesis of L-Indospicine, [5,5,6-2H3 ]- L-Indospicine and L-Norindospicine
Journal name Organic and Biomolecular Chemistry   Check publisher's open access policy
ISSN 1477-0520
1477-0539
Publication date 2016-01-01
Year available 2016
Sub-type Article (original research)
DOI 10.1039/C6OB01187J
Open Access Status Not Open Access
Volume 14
Issue 28
Start page 6826
End page 6832
Total pages 7
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Language eng
Subject 1303 Biochemistry
1606 Physical and Theoretical Chemistry
1605 Organic Chemistry
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.
Formatted 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.
Keyword Biochemistry & Molecular Biology
Chemistry, Organic
Biochemistry & Molecular Biology
Chemistry
Q-Index Code C1
Q-Index Status Provisional Code
Grant ID B.AHE.0042
Institutional Status UQ

 
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Created: Tue, 28 Jun 2016, 08:56:40 EST by Dr Mary Fletcher on behalf of School of Chemistry & Molecular Biosciences