Total Synthesis of WS9326A, a Potent Tachykinin Antagonist from Streptomyces violaceoniger
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概要
- 論文の詳細を見る
Total synthesis of the cyclic peptide lactone WS9326A, a potent tachykinin antagonist isolated from Streptomyces violaceoniger strain 9326,has been achieved via Cbz-Thr(Boc-allo-Thr-Asn-Ser(Bzl))-(E)ΔMeTyr-Leu-D-Phe-OTce, which was cyclized (Phe and allo-Thr) using an active ester method with N-hydroxysuccinimide. Finally the unique N-acyl group, the 2-(1(Z)-pentenyl)cinnamoyl moiety, was introduced onto the amino group in the Thr unit. The key step of the synthesis involves the preparation of the E-isomer of the dehydro-N-mehyltyrosine (ΔMeTyr) unit. The debenzoxylation reaction of the threo- and erythro-isomers of β-benzoxy-N-methyltyrosine drivatives gave exclusively the Z-isomer of Cbz-Thr-ΔMeTyr(MOM)-OMe, which was then converted to the desired E-isomer by photochemical isomerization of Cbz-Thr(TBDMS)-(Z)ΔMeTyr(MOM)-Leu-D-Phe-OTce at a later step.
- 公益社団法人日本薬学会の論文
- 1997-02-15
著者
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Tanaka H
Faculty Of Pharmacy Meijo University
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Okada S
School Of Pharmaceutical Sciences University Of Shizuoka
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Okada S
Exploratory Research Laboratories Fujisawa Pharmaceutical Co. Ltd.
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Tanaka H
Department Of Bioresources Chemistry Faculty Of Agriculture Okayama University
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Tanaka H
Exploratory Research Laboratories Fujisawa Pharmaceutical Co. Ltd.
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OKADA Satoshi
Exploratory Research Laboratories, Fujisawa Pharmaceutical Co., Ltd.,
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TANAKA Hirokazu
Exploratory Research Laboratories, Fujisawa Pharmaceutical Co., Ltd.
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SHIGEMATSU Nobuharu
Exploratory Research Laboratories, Fujisawa Pharmaceutical Co., Ltd.,
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KAYAKIRI Natsuko
Exploratory Research Laboratories, Fujisawa Pharmaceutical Co., Ltd.,
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岡田 昌二
静岡県大
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Toyama Hirohide
Institute For Chemical Research Kyoto University
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Tanaka Haruyuki
Chemical Branch Faculty Of Engineering And Kansai University High Technology Research Center Kansai
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Shigematsu N
Exploratory Research Laboratories Fujisawa Pharmaceutical Co. Ltd.
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Shigematsu Nobuharu
Exploratory Research Laboratories Fujisawa Pharmaceutical Co. Ltd.
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Okada Satoshi
Exploratory Research Laboratories Fujiawa Pharmaceutical Co. Ltd.
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Tanaka Hirokazu
Exploratory Research Laboratories Fujisawa Pharmaceutical Co. Ltd.
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Shigematsu Nobuharu
Exploratory Research Division Astellas Research Technologies
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TANAKA Hiromi
Department of Physics Faculty of Education, Saga University
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