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The Twisted Side Chain of Antillatoxin is Important for Potent Toxicity: Total Synthesis and Biological Evaluation of Antillatoxin and Analogues
Author(s) -
Okura Ken,
Matsuoka Shigeru,
Goto Ryosuke,
Inoue Masayuki
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200905892
Subject(s) - side chain , chemistry , cytotoxicity , biological activity , stereochemistry , peptide , toxicity , chain (unit) , combinatorial chemistry , biochemistry , in vitro , organic chemistry , polymer , physics , astronomy
Side‐chain plays lead role : Antillatoxin is a cyclic peptide and potent neurotoxin, and the total syntheses and biological evaluations of antillatoxin and its side‐chain analogues are reported. A subtle side‐chain modification led to dramatic changes in the cytotoxicity; detailed conformational analyses revealed that the shape of the twisted side chain is critical for the biological activity of antillatoxin.