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Site-Selective Construction of N-Linked Glycopeptides through Photoredox Catalysis

文献类型：期刊论文

作者Wei, Bingcheng5; Huang, Ping2,3,5; Wang, Xinyao1; Liu, Zhi4; Tang, Feng4; Huang, Wei4; Liu, Bing1; Ye, Farong5; Wang, Ping2,3,5
刊名ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
出版日期2024-11-12
页码8
关键词Photoredox Catalysis Dehydroalanine Glycopeptide
ISSN号1433-7851
DOI10.1002/anie.202415565
英文摘要The glycosylation of peptides and proteins can significantly impact their intrinsic properties, such as conformation, stability, antigenicity, and immunogenicity. Current methods for preparing N-linked glycopeptides typically rely on amide bond formation, which can be limited by the presence of reactive functional groups like acids and amines. Late-stage functionalization of peptides offers a promising approach to obtaining N-linked glycopeptides. In this study, we demonstrate the preparation of N-linked glycopeptides through a photoredox-catalyzed site-selective Giese addition between N-glycosyl oxamic acid and peptides containing dehydroalanine (Dha) under visible light conditions. Unlike traditional methods that rely on the coupling of aspartic acid and glycosylamine, this approach utilizes the conjugation of N-glycosylated carbamoyl radicals with Dha, facilitating the straightforward modification of complex peptides.
WOS关键词CHEMICAL-SYNTHESIS ; AMINO-ACIDS ; DEHYDROALANINE ; PEPTIDES ; ACTIVATION ; INSTALLATION ; CONVERSION ; CYSTEINES ; ADDITIONS ; PROTEINS
资助项目National Natural Science Foundation of China[92253302] ; National Natural Science Foundation of China[22225701] ; National Natural Science Foundation of China[22077080] ; National Natural Science Foundation of China[22477078] ; National Science Fund for National Natural Science Foundation of China[21TQ1400210] ; Shanghai Pilot Program for Basic Research-Shanghai Jiao Tong University[20230102] ; Interdisciplinary Program of Shanghai Jiao Tong University ; Shanghai Municipal Science and Technology Major Project ; Department of Human Resources, and Social Security of Sichuan Province
WOS研究方向Chemistry
WOS记录号WOS:001356934300001
出版者WILEY-V C H VERLAG GMBH
源URL[http://119.78.100.183/handle/2S10ELR8/314539]  
专题新药研究国家重点实验室
通讯作者Huang, Ping; Ye, Farong; Wang, Ping
作者单位1.Harbin Med Univ, Affiliated Hosp 1, Dept Oral & Maxillofacial Surg, Harbin 150001, Peoples R China
2.Shanghai Jiao Tong Univ, Sichuan Res Inst, Chengdu 610213, Peoples R China
3.Shanghai Jiao Tong Univ, Sch Pharmaceut Sci, Natl Key Lab Innovat Immunotherapy, Shanghai 200240, Peoples R China
4.Chinese Acad Sci, Shanghai Inst Mat Med, Ctr Biotherapeut Discovery Res, State Key Lab Drug Res, Shanghai 201203, Peoples R China
5.Shanghai Jiao Tong Univ, Zhang jiang Inst Adv Study, Ctr Chem Glycobiol, Sch Chem & Chem Engn,Shanghai Key Lab Mol Engn Chi, Shanghai 200240, Peoples R China
推荐引用方式
GB/T 7714		 Wei, Bingcheng,Huang, Ping,Wang, Xinyao,et al. Site-Selective Construction of N-Linked Glycopeptides through Photoredox Catalysis[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2024:8.
APA Wei, Bingcheng.,Huang, Ping.,Wang, Xinyao.,Liu, Zhi.,Tang, Feng.,...&Wang, Ping.(2024).Site-Selective Construction of N-Linked Glycopeptides through Photoredox Catalysis.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,8.
MLA Wei, Bingcheng,et al."Site-Selective Construction of N-Linked Glycopeptides through Photoredox Catalysis".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2024):8.

入库方式： OAI收割

来源：上海药物研究所

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