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Synthesis 2009(13): 2184-2204  
DOI: 10.1055/s-0029-1216837
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Four Lysine-Linked Cereulide Analogues Showing Ionophoric Activity Towards Potassium Cations as Lead Compounds for Emetic Toxin-Detection by Immunoassays

Arthit Makarasena, Toshio Nishikawaa, Minoru Isobe*a,b
a Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan
b Institute for Advanced Research, Nagoya University, Chikusa, Nagoya 464-8601, Japan
e-Mail: isobem@agr.nagoya-u.ac.jp; e-Mail: minoru@mx.nthu.edu.tw;
Further Information

Publication History

Received 22 January 2009
Publication Date:
25 May 2009 (online)

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Abstract

An improved total synthesis of the emetic toxin cereulide and the preparation of four lysine-linked cereulide analogues is described. The cereulide analogues are prepared by replacing one of the amino acid residues in cereulide with lysine. The cereulide analogues demonstrate ionophoric activity towards alkali metal ions and inorganic ammonium ions, and are currently being used to develop an enzyme-linked immunosorbent assay for cereulide.

Key words

cereulide - Bacillus cereus - peptide synthesis - ionophore - l-O-lysine

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