Concurrent modifications of the C-terminus and side ring of thiostrepton and their synergistic effects with respect to improving antibacterial activities

Shoufeng Wang; Qingfei Zheng; Jianfeng Wang; Dandan Chen; Yunsong Yu; Wen Liu

doi:10.1039/C5QO00433K

Concurrent modifications of the C-terminus and side ring of thiostrepton and their synergistic effects with respect to improving antibacterial activities†

Shoufeng Wang,‡*^a Qingfei Zheng,‡^a Jianfeng Wang,^b Dandan Chen,^c Yunsong Yu^b and Wen Liu*^ac

* Corresponding authors

^a State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
E-mail: wangshoufeng@sioc.ac.cn
Tel: +86-21-54925539

^b Department of Infectious Diseases, Sir Run Run Shaw Hospital, College of Medicine, Zhejiang University, Hangzhou, Zhejiang 310016, China

^c Huzhou Center of Bio-Synthetic Innovation, 1366 Hongfeng Road, Huzhou 313000, China
E-mail: wliu@mail.sioc.ac.cn
Tel: +86-21-54925111

Abstract

The double-mutant strain Streptomyces laurentii ΔtsrB/T was designed and constructed based on a recent understanding regarding the structure–activity relationship of thiostrepton (TSR) against prokaryotic pathogens. Five new C-terminally methylated TSR (CmTSR) derivatives that varied in the side-ring structure were obtained via the chemical feeding of quinaldic acid (QA) analogs. These derivatives provide new insights into the tolerance of QA incorporation in TSR biosynthesis. Certain members of the tested TSR derivatives, meanwhile, exhibited much better antibacterial activities than all currently known thiopeptide antibiotics.

This article is part of the themed collection: Celebrating 70 Years of Shanghai Institute of Organic Chemistry

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DOI: https://doi.org/10.1039/C5QO00433K
Article type: Research Article
Submitted: 22 Dec 2015
Accepted: 08 Feb 2016
First published: 09 Feb 2016

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Org. Chem. Front., 2016,3, 496-500

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Concurrent modifications of the C-terminus and side ring of thiostrepton and their synergistic effects with respect to improving antibacterial activities

S. Wang, Q. Zheng, J. Wang, D. Chen, Y. Yu and W. Liu, Org. Chem. Front., 2016, 3, 496 DOI: 10.1039/C5QO00433K

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Concurrent modifications of the C-terminus and side ring of thiostrepton and their synergistic effects with respect to improving antibacterial activities†

Abstract

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Concurrent modifications of the C-terminus and side ring of thiostrepton and their synergistic effects with respect to improving antibacterial activities

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