Solid Phase Synthesis of Isariin, a Long Chain β-Hydroxy Acid-containing Cyclodepsipeptide, and Its Diastereoisomer

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概要

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• The method of solid phase synthesis was applied to the preparation of isariin (Ia), a β-hydroxydodecanoic acid-containing cyclodepsipeptide metabolite of Isaria cretacea, and its isomer (Ib). The open-chain depsipeptide, H-Val-D-Leu-Ala-Val-DL-Hyd-Gly-OH, was synthesized by coupling successively BOC-Val-DL-Hyd-OH, alanine, and Z-Val-D-Leu-OH to resin-bound glycine using dicyclohexylcarbodiimide (DCC) or DCC+hydroxysuccinimide (HOSu) as coupling agent. After cleavage from the resin the depsipeptide was cyclized by means of DCC+HOSu. The cyclization product was successfully resolved, after chromatographic purification on Dowex 50×4 and Sephadex LH-20 column, by preparative thin-layer chromatography on silica gel to afford Ia and Ib in moderate yields.

• 公益社団法人日本薬学会の論文
• 1974-09-25

著者

• 平本 実

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 岡田 幸蔵

  近畿大学薬学部

• 岡田 幸蔵

  Faculty Of Pharmaceutical Science Kinki University

• 黒沢 陽太郎

  Kissei Yakuhin Co., Ltd.

• 黒沢 陽太郎

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 平本 実

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 黒沢 陽太郎

  Kissei Yakuhin Co. Ltd.

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