52 ジョロウグモNephila clavataの神経毒Nephilatoxin類の合成研究 : Nephilatoxin-9および11の全合成(口頭発表の部)

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Nephilatoxins (NPTX-1-12), recently isolated from the venom of Joro spider (Nephila clavata), have been characterized as a new type of spider toxins possessing an indole-3-acetyl moiety linked with N-termini of the polycationic part composed of basic amino acids and polyamines. The toxins induce histamine release from rat peritoneal mast cells and some of the toxins act as a potent blocker of glutamatergic nerve in the lobster leg. We report herein the total synthesis of NPTX-9, the most potent glutamate receptor antagonist among Nephilatoxins, as well as NPTX-11 and NPTX-12. The key feature of the present synthesis lies in the employment of 1-azido-5-N-Boc-aminopentane (4) as cadaverine (1,5-diaminopentane) unit, which could efficiently be prepared from commercially available 5-aminopentanol (1) in the three steps (Scheme 1). Similarly, putreanine (8-amino-4-azaoctanoic acid) which is the most common polyamine unit in the spider toxins, was introduced using azide derivative 9 (Scheme 2). Synthetic Nephilatoxins were identical with the natural compounds (HPLC, FAB-MS, NMR) and exhibited similar blocking action of the glutamatergic nerve to that of the latter.
天然有機化合物討論会の論文
1990-09-25