Total Syntheses of Streptamidine and Klebsazolicin Using Biomimetic On‐Resin Ring‐Closing Amidine Formation

Author:

Liu Shunhe1,Tang Yang2,Chen Sheng3,Li Xuechen14ORCID,Liu Han1

Affiliation:

1. Department of Chemistry State Key Laboratory of Synthetic Chemistry The University of Hong Kong Pokfulam Road Hong Kong SAR P. R. China

2. Department of Infectious Diseases and Public Health Jockey Club College of Veterinary Medicine and Life Sciences City University of Hong Kong Kowloon Hong Kong SAR P. R. China

3. Department of Food Science and Nutrition State Key Lab of Chemical Biology and Drug Discovery The Hong Kong Polytechnic University Hung Hom, Kowloon Hong Kong SAR P. R. China

4. Laboratory for Marine Drugs and Bioproducts Qingdao Marine Science and Technology Center School of Medicine and Pharmacy Ocean University of China Qingdao, 266003 P. R. China

Abstract

AbstractDiketopiperazine (DKP) derived cyclic amidine structures widely exist in peptide natural products according to the genome mining result. The largely unknown bioactivity and mode of action are partially caused by the poor availability of the compounds via microbiological and chemical approaches. To tackle this challenge, in this work, we have developed the on‐resin ring‐closing amidine formation strategy to synthesize peptides containing N‐terminal DKP derived cyclic amidine structure, in which the 6‐exo‐trig cyclization mediated by HgCl2 activation of thioamides was the key step. Leveraging from this new strategy, we finished the total syntheses of streptamidine and klebsazolicin. Meanwhile, eleven klebsazolicin analogues were synthesized for its structure–activity relationship study.

Funder

Research Grants Council, University Grants Committee

Publisher

Wiley

同舟云学术

1.学者识别学者识别

2.学术分析学术分析

3.人才评估人才评估

"同舟云学术"是以全球学者为主线,采集、加工和组织学术论文而形成的新型学术文献查询和分析系统,可以对全球学者进行文献检索和人才价值评估。用户可以通过关注某些学科领域的顶尖人物而持续追踪该领域的学科进展和研究前沿。经过近期的数据扩容,当前同舟云学术共收录了国内外主流学术期刊6万余种,收集的期刊论文及会议论文总量共计约1.5亿篇,并以每天添加12000余篇中外论文的速度递增。我们也可以为用户提供个性化、定制化的学者数据。欢迎来电咨询!咨询电话:010-8811{复制后删除}0370

www.globalauthorid.com

TOP

Copyright © 2019-2024 北京同舟云网络信息技术有限公司
京公网安备11010802033243号  京ICP备18003416号-3