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Synthesis of Disulfide Surrogate Peptides Incorporating Large-Span Surrogate Bridges Through a Native-Chemical-Ligation-Assisted Diaminodiacid Strategy

文献类型：期刊论文

作者Qu, Qian1; Gao, Shuai1; Wu, Fangming3; Zhang, Meng-Ge2; Li, Ying2; Zhang, Long-Hua2; Bierer, Donald4; Tian, Chang-Lin2,3; Zheng, Ji-Shen2; Liu, Lei1
刊名ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
出版日期2020-04-06
卷号59
ISSN号1433-7851
关键词chemical protein synthesis cyclic peptides disulfides native chemical ligation peptides
DOI10.1002/anie.201915358
通讯作者Tian, Chang-Lin(cltian@ustc.edu.cn) ; Zheng, Ji-Shen(jszheng@ustc.edu.cn) ; Liu, Lei(lliu@mail.tsinghua.edu.cn)
英文摘要The use of synthetic bridges as surrogates for disulfide bonds has emerged as a practical strategy to obviate the poor stability of some disulfide-containing peptides. However, peptides incorporating large-span synthetic bridges are still beyond the reach of existing methods. Herein, we report a native chemical ligation (NCL)-assisted diaminodiacid (DADA) strategy that enables the robust generation of disulfide surrogate peptides incorporating surrogate bridges up to 50 amino acids in length. This strategy provides access to some highly desirable but otherwise impossible-to-obtain disulfide surrogates of bioactive peptide. The bioactivities and structures of the synthetic disulfide surrogates were verified by voltage clamp assays, NMR, and X-ray crystallography; and stability studies established that the disulfide replacements effectively overcame the problems of disulfide reduction and scrambling that often plague these pharmacologically important peptides.
WOS关键词SOLID-PHASE SYNTHESIS ; ALPHA-CONOTOXIN ; CYCLIC-PEPTIDES ; PROTEINS ; ANALOGS ; DISCOVERY ; CYSTEINE ; TOXIN ; IMI
资助项目National Key R&D Program of China[2017YFA0505200] ; National Key R&D Program of China[2019YFA0706902] ; NSFC[21532004] ; NSFC[91753205] ; NSFC[81621002] ; NSFC[U1732161] ; NSFC[91753120] ; NSFC[21825703] ; NSFC[U1732275] ; NSFC[21927814] ; CAS[XDB08030302] ; Science and Technological Fund of Anhui Province for Outstanding Youth[1808085J04] ; High Magnetic Field Laboratory of Anhui Province
WOS研究方向Chemistry
语种英语
出版者WILEY-V C H VERLAG GMBH
WOS记录号WOS:000519963000001
资助机构National Key R&D Program of China ; NSFC ; CAS ; Science and Technological Fund of Anhui Province for Outstanding Youth ; High Magnetic Field Laboratory of Anhui Province
源URL[http://ir.hfcas.ac.cn:8080/handle/334002/103801]  
专题中国科学院合肥物质科学研究院
通讯作者Tian, Chang-Lin; Zheng, Ji-Shen; Liu, Lei
作者单位1.Tsinghua Univ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Ctr Synthet & Syst Biol,Dept Chem, Tsinghua Peking Ctr Life Sci,Minist Educ, Beijing 100084, Peoples R China
2.Univ Sci & Technol China, Sch Life Sci, Hefei Natl Lab Phys Sci Microscale, Hefei 230027, Peoples R China
3.Chinese Acad Sci, High Field Magnet Lab, Hefei 230031, Peoples R China
4.Bayer AG, Dept Med Chem, Aprather Weg 18A, D-42096 Wuppertal, Germany
推荐引用方式
GB/T 7714		 Qu, Qian,Gao, Shuai,Wu, Fangming,et al. Synthesis of Disulfide Surrogate Peptides Incorporating Large-Span Surrogate Bridges Through a Native-Chemical-Ligation-Assisted Diaminodiacid Strategy[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2020,59.
APA Qu, Qian.,Gao, Shuai.,Wu, Fangming.,Zhang, Meng-Ge.,Li, Ying.,...&Liu, Lei.(2020).Synthesis of Disulfide Surrogate Peptides Incorporating Large-Span Surrogate Bridges Through a Native-Chemical-Ligation-Assisted Diaminodiacid Strategy.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,59.
MLA Qu, Qian,et al."Synthesis of Disulfide Surrogate Peptides Incorporating Large-Span Surrogate Bridges Through a Native-Chemical-Ligation-Assisted Diaminodiacid Strategy".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 59(2020).

入库方式： OAI收割

来源：合肥物质科学研究院

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