Cyclic peptides. XII. Synthesis of AM-toxin III and its analogs.

Abstract

A cyclic tetradepsipeptide with a sequence corresponding to AM-toxin III (a phytotoxic peptide) was synthesized by a conventional method in order to confirm the proposed structure. This was mediated through a deamination reaction of precursor cyclotetradepsipeptide containing a D-2, 3-diaminopropionic acid residue by the Hofmann degradation method. The synthetic peptide and natural AM-toxin III were identical in regard to t.l.c., crystal form, mass spectrum and biological activity in causing necrosis on apple leaves. Two analogs, [l-O-methyl-L-tyrosine]-AM-toxin and [l-L-tyrosine]-AM-toxin showed extremely weak activity; the relationship between the bulkiness of an aromatic side chain at position 1 of AM-toxin III and its biological activity is discussed.

• Authors: T Kanmera, N Izumiya
• Journal: International journal of peptide and protein research (Int J Pept Protein Res) Vol. 19 Issue 1 Pg. 79-87 (Jan 1982) ISSN: 0367-8377 [Print] Denmark
• PMID: 7118384 (Publication Type: Comparative Study, Journal Article)

Chemical References

• Mycotoxins
• Peptides, Cyclic
• AM toxin III

Topics

• Chemical Phenomena
• Chemistry
• Chromatography, Thin Layer
• Crystallization
• Mass Spectrometry
• Methods
• Mycotoxins (chemical synthesis)
• Peptides, Cyclic (chemical synthesis, pharmacology)
• Plants (drug effects)
• Structure-Activity Relationship