Cyclic peptides. V. Synthesis of AM-toxin II and its analog.

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.

• Authors: Y Shimohigashi, N Izumiya
• Journal: International journal of peptide and protein research (Int J Pept Protein Res) Vol. 12 Issue 1 Pg. 7-16 (Jul 1978) ISSN: 0367-8377 [Print] Denmark
• PMID: 681086 (Publication Type: Journal Article)

Chemical References

• Peptide Fragments
• Peptides, Cyclic
• Toxins, Biological

Topics

• Amino Acid Sequence
• Biological Assay
• Chemical Phenomena
• Chemistry
• Peptide Fragments
• Peptides, Cyclic (chemical synthesis, pharmacology)
• Toxins, Biological (chemical synthesis, pharmacology)