Cyclic peptides. IV. Synthesis of diastereomeric dihydro-AM-toxin I and its analogs.

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概要

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• Diastereomeric cyclotetradepsipeptides [L-Ala<SUP>2</SUP>]– and [D-Ala<SUP>2</SUP>]–AM-toxin I, corresponding to the hydrogenated products of AM-toxin I, were synthesized by the conventional method and their biological activities were tested. [D-Ala<SUP>2</SUP>]–AM-toxin I exhibits weak but recognizable necrotic activity (5–10 μg/ml) on apple leaves. [L-Ala<SUP>2</SUP>]–AM-toxin I is inactive even in a high concentration of 100 μ/ml. The results of NMR and ORD measurements of [D-Ala<SUP>2</SUP>]–AM-toxin I and [L-Tyr(Me)<SUP>1</SUP>, D-Ala<SUP>2</SUP>]–AM-toxin indicates the presence of a common conformer. The results on [L-Ala<SUP>2</SUP>]–AM-toxin I and [L-Tyr(Me)<SUP>1</SUP>, L-Ala<SUP>2</SUP>]–AM-toxin revealed the presence of more than two conformers, the predominant conformation differing from that of D-isomers. Difference in activity between [D-Ala<SUP>2</SUP>]– and [L-Ala<SUP>2</SUP>]–AM-toxin I can be attributed to the difference in conformation of the diastereomers.

• 公益社団法人 日本化学会の論文

著者

• Shimohigashi Yasuyuki

  Laboratory Of Biochemistry Department Of Chemistry Faculty Of Science Kyushu University

• Lee Sannamu

  Laboratory Of Biochemistry Faculty Of Science Kyushu University

• Izumiya Nobuo

  Laboratory Of Biochemistry Faculty Of Engineering Kyushu Sangyo University

• Lee Sannamu

  Laboratory of Biochemistry, Faculty of Science 33, Kyushu University

• Kato Tetsuo

  Laboratory of Biochemistry, Faculty of Science 33, Kyushu University

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