45 AM-Toxin Iとそのアナローグの合成

概要

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Synthesis of a cyclotetradepsipeptide corresponding to the sequence, cyclo(-L-Amv-Dha-L-Ala-L-Hyv-)(1), of AM-Toxin I was designed by a solution method in peptide synthesis (Amv, α-amino-δ-p-methoxyphenyl-valeric acid). For a preliminary experiment, [O-Me-L-Tyr]-AM-Toxin I(2) was selected as a model peptide. Synthesis of 2 was attempted through three different routes, and the one afforded a desired peptide corresponding 2. The synthetic route involved the cyclization of H-L-Ser-L-Ala-L-Hyv-L-Tyr(Me)-OSu, and subsequent conversion of the L-Ser into Dha by treatment with diethylamine. The L-Amv was prepared in good yield by optical resolution of acetyl-DL-Amv with Taka-acylase. Synthesis of a peptide corresponding to 1 was achieved by the same route, and the peptide obtained was identical with the natural Toxin I in regard to TLC, UV, MS and biological activity. By the data of biological activities of synthetic several cyclodepsipeptides including 2, monomers, and dimers, the relationship between structure and function was discussed.
天然有機化合物討論会の論文
1975-10-01