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The Orientation of the Terminal t Bu Group of Antillatoxin is Important for Potent Toxicity: Design, Synthesis and Biological Evaluation of Conformationally Restricted Analogues of Antillatoxin
Author(s) -
Okura Ken,
Inoue Masayuki
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300111
Subject(s) - chemistry , stereochemistry , terminal (telecommunication) , orientation (vector space) , toxicity , group (periodic table) , combinatorial chemistry , organic chemistry , geometry , telecommunications , mathematics , computer science
What′s your poison? Antillatoxin is a cyclic peptide and a potent cytotoxin. We designed two epimeric C8,C9‐dihydroantillatoxins in which the t Bu‐substituted side‐chain of antillatoxin is conformationally restricted without changing the overall shape and chemical properties of the molecule. Structural and biological studies of antillatoxin and the two dihydroantillatoxins uncovered the orientation of the terminal t Bu group that is crucial for its potent toxicity.