Syntheses of AM-toxin III and its analogs using the Hofmann degradation

✍ Scribed by Tatsuhiko Kanmera; Haruhiko Aoyagi; Michinori Waki; Tetsuo Kato; Nobuo Izumiya; Kosaku Noda; Tamio Ueno

• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 241 KB
• Volume: 22
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)81977-8

✦ Synopsis

Syntheses of cyclotetradepsipeptides, AM-toxin 111 and two analogs, were achieved, in which the Hofmann degradation method was used in order to derive a dehydroalanine residue from a 2,3_diaminopropionic acid residue in cyclodepsipeptide precursors.

AM-Toxins (Fig. 1) are host-specific phytotoxic metabolites produced by AZtermaria mati, which cause leaf spot disease of apple. l-3) Previously, we reported the confirmation of the structure of AM-toxin I and II by their chemical syntheses.

4,5)

The structure of AM-toxin III Res., lo, 197 (1977).

Protein

8. Satisfactory elemental analyses and chromatographic data were obtained for all crystalline compounds. 9) Molecular weight was determined on Nihondenshi mass spectrometer JMS-OlSG-2.