CYCLIC PEPTIDES

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Abstract
A cyclic tetradepsipeptide with a sequence corresponding to AM‐toxin II (a phytotoxic peptide) was synthesized in order to confirm the proposed structure by a conventional method. This was mediated through a dehydration reaction of cyclodepsipeptide containing a D‐Ser residue, by methanesulfonyl chloride containing sulfur dioxide. The synthetic peptide and natural AM‐toxin II were identical as regards t.l.c, crystal form, several kinds of spectra measurements and biological activity in causing necrosis on apple leaves. An analog, [L‐Phe1]‐AM‐toxin, containing the lower homolog (L‐phenylalanine) instead of L‐2‐amino‐5‐phenylpentanoic acid in position 1 of natural toxin II, was synthesized simultaneously. [L‐Phe1] ‐AM‐toxin showed extremely weak activity; the relationship between the bulkiness of an aromatic side chain and the biological activity of AM‐toxin II is discussed.

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