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52 SYNTHETIC STUDIES ON NEPHILATOXINS, NEUROTOXINS OF JORO SPIDER (NEPHILA CLAVATA) : TOTAL SYNTHESIS OF NEPHILATOXINS-9 AND 11
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- Miyashita M.
- Chemical Research Institute of Non-Aqueous Solutions, Tohoku University
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- Sato H.
- Chemical Research Institute of Non-Aqueous Solutions, Tohoku University
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- Yoshikoshi A.
- Chemical Research Institute of Non-Aqueous Solutions, Tohoku University
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- Toki T.
- Research Center, Daicel Chemical Industries LTD.
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- Yanami T.
- Research Center, Daicel Chemical Industries LTD.
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- Kikuchi Y.
- Department of Chemistry, Tohoku University
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- Takasaki C.
- Department of Chemistry, Tohoku University
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- Nakajima T.
- Department of Analytical Chemistry, University of Tokyo
Bibliographic Information
- Other Title
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- 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)
Description
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.
Journal
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- Symposium on the Chemistry of Natural Products, symposium papers
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Symposium on the Chemistry of Natural Products, symposium papers 32 (0), 388-395, 1990
Symposium on the Chemistry of Natural Products Steering Committee
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Details 詳細情報について
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- CRID
- 1390282681051438208
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- NII Article ID
- 110006678925
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- ISSN
- 24331856
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- Text Lang
- ja
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- Data Source
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- JaLC
- CiNii Articles
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- Abstract License Flag
- Disallowed