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First total synthesis of hoshinoamide A.

ABSTRACT: Hoshinoamides A, B and C, linear lipopeptides, were isolated from the marine cyanobacterium Caldora penicillata, with potent antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum. Herein, we describe the first total synthesis of hoshinoamide A by the combination of liquid-phase and solid-phase peptide synthesis. Liquid-phase synthesis is to improve the coupling yield of ʟ-Val³ and N-Me-ᴅ-Phe². Connecting other amino acids efficiency and convergence is achieved by solid-state synthesis. Our synthetic strategy could synthesize the target peptide in high yield with good purity.

SUBMITTER: Zhou H

PROVIDER: S-EPMC8685559 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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First total synthesis of hoshinoamide A.

Zhou Haipin H Rui Zihan Z Yang Yiming Y Xu Shengtao S Shao Yutian Y Liu Long L

Beilstein journal of organic chemistry 20211215

Hoshinoamides A, B and C, linear lipopeptides, were isolated from the marine cyanobacterium Caldora penicillata, with potent antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum. Herein, we describe the first total synthesis of hoshinoamide A by the combination of liquid-phase and solid-phase peptide synthesis. Liquid-phase synthesis is to improve the coupling yield of ʟ-Val3 and N-Me-ᴅ-Phe2. Connecting other amino acids efficienc ...[more]

PMID: 34956412

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