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Chemical synthesis and biological activity of peptides incorporating an ether bridge as a surrogate for a disulfide bond

文献类型：期刊论文

作者Zhao, Rui1,3; Shi, Pan3; Chen, Junyou1; Sun, Shuaishuai1; Chen, Jingnan1; Cui, Jibin1; Wu, Fangming6; Fang, Gemin5; Tian, Changlin3; Shi, Jing3
刊名CHEMICAL SCIENCE
出版日期2020-08-14
卷号11
ISSN号2041-6520
DOI10.1039/d0sc02374d
通讯作者Shi, Jing(shijing@ustc.edu.cn) ; Li, Yi-Ming(ymli@hfut.edu.cn)
英文摘要Disulfide bridges contribute to the definition and rigidity of polypeptides, but they are inherently unstable in reducing environments and in the presence of isomerases and nucleophiles. Strategies to address these deficiencies, ideally without significantly perturbing the structure of the polypeptide, would be of great interest. One possible surrogate for the disulfide bridge is a simple thioether, but these are susceptible to oxidation. We report the introduction of an ether linkage into the biologically active, disulfide-rich peptides oxytocin, tachyplesin I, and conotoxin alpha-ImI, using an ether-containing diaminodiacid as the key building block, obtained by the stereoselective ring-opening addition reaction of an aziridine skeleton with a hydroxy group. NMR studies indicated that the derivatives with an ether surrogate bridge exhibited very small change of their three-dimensional structures. The analogs obtained using this novel substitution strategy were found to be more stable than the original peptide in oxidative and reductive conditions; without a loss of bioactivity. This strategy is therefore proposed as a practical and versatile solution to the stability problems associated with cysteine-rich peptides.
WOS关键词SOLID-PHASE SYNTHESIS ; ALPHA-CONOTOXIN ; EFFICIENT SYNTHESIS ; REPLACEMENT ; TACHYPLESIN ; AZIRIDINES ; HELICITY ; PROTEINS ; ANALOGS ; CYSTINE
资助项目National Key R&D Program of China[2017YFA0505400] ; National Key R&D Program of China[2017YFA0505200] ; National Natural Science Foundation of China[91753205] ; National Natural Science Foundation of China[21877024] ; National Natural Science Foundation of China[21977089] ; National Natural Science Foundation of China[81621002] ; National Natural Science Foundation of China[31971152] ; National Natural Science Foundation of China[21621003] ; Fundamental Research Funds for the Central Universities[JZ2019HGPB0105]
WOS研究方向Chemistry
语种英语
出版者ROYAL SOC CHEMISTRY
WOS记录号WOS:000555801800018
资助机构National Key R&D Program of China ; National Natural Science Foundation of China ; Fundamental Research Funds for the Central Universities
源URL[http://ir.hfcas.ac.cn:8080/handle/334002/44927]  
专题中国科学院合肥物质科学研究院
通讯作者Shi, Jing; Li, Yi-Ming
作者单位1.Hefei Univ Technol, Sch Food & Biol Engn, Hefei 230009, Anhui, Peoples R China
2.Tsinghua Univ, Dept Chem, Beijing 100084, Peoples R China
3.Univ Sci & Technol China, Sch Life Sci, Dept Chem, Hefei Natl Lab Phys Sci Microscale, Hefei 230009, Anhui, Peoples R China
4.Bayer AG, Dept Med Chem, Aprather Weg 18A, D-4206 Wuppertal, Germany
5.Anhui Univ, Sch Life Sci, Inst Phys Sci & Informat Technol, Hefei 230601, Peoples R China
6.Chinese Acad Sci, High Magnet Field Lab, Hefei 230031, Peoples R China
推荐引用方式
GB/T 7714		 Zhao, Rui,Shi, Pan,Chen, Junyou,et al. Chemical synthesis and biological activity of peptides incorporating an ether bridge as a surrogate for a disulfide bond[J]. CHEMICAL SCIENCE,2020,11.
APA Zhao, Rui.,Shi, Pan.,Chen, Junyou.,Sun, Shuaishuai.,Chen, Jingnan.,...&Li, Yi-Ming.(2020).Chemical synthesis and biological activity of peptides incorporating an ether bridge as a surrogate for a disulfide bond.CHEMICAL SCIENCE,11.
MLA Zhao, Rui,et al."Chemical synthesis and biological activity of peptides incorporating an ether bridge as a surrogate for a disulfide bond".CHEMICAL SCIENCE 11(2020).

入库方式： OAI收割

来源：合肥物质科学研究院

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