Total Synthesis of WS9326A, a Potent Tachykinin Antagonist from Streptomyces violaceoniger.
書誌事項
- タイトル別名
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- Total Synthesis of WS9326A a Potent Tac
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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.
収録刊行物
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- ＣＨＥＭＩＣＡＬ ＆ ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ ＢＵＬＬＥＴＩＮ
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ＣＨＥＭＩＣＡＬ ＆ ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ ＢＵＬＬＥＴＩＮ 45 (2), 236-242, 1997
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390282679140472192
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- NII論文ID
- 130003773701
- 110003616463
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- NII書誌ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL書誌ID
- 4163492
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- PubMed
- 9118439
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可