First total synthesis of hoshinoamide A

Haipin Zhou; Zihan Rui; Yiming Yang; Shengtao Xu; Yutian Shao; Long Liu

doi:10.3762/bjoc.17.201

First total synthesis of hoshinoamide A

Beilstein J Org Chem. 2021 Dec 15:17:2924-2931. doi: 10.3762/bjoc.17.201. eCollection 2021.

Authors

Haipin Zhou¹, Zihan Rui¹, Yiming Yang¹, Shengtao Xu^{1

2}, Yutian Shao¹, Long Liu³

Affiliations

¹ College of Materials & Chemical Engineering, Chuzhou University, Chuzhou 239000, China.
² State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, China Pharmaceutical University,24 Tong Jia Xiang, Nanjing 210009, China.
³ Taizhou Medical Hi-Tech Development Public Services Platform, Taizhou 225300, China.

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.

Keywords: antimalarial; highly methylated polypeptides; hoshinoamides; total synthesis.

Grants and funding

This research was supported by the Natural Science key Project of Anhui Education Department (Grant No. KJ2019A0635); Provincial University Students’ Innovation and Entrepreneurship Program (Grant No. 2019CXXL077); Hubei Province Key Laboratory of Occupational Hazard Identification and Control, Wuhan University of Science and Technology (Grant No. OHIC2020Y06).