Functionalization of amino acids with aryl fluorosulfate for prodrug construction by SuFEx chemistry

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成果类型：

期刊论文

作者：

Luo, Xingrui;Pailla, Santhosh Kumar;Gao, Fei;Zheng, Xing*;Wang, Ruowen*

通讯作者：

Zheng, Xing;Wang, Ruowen

作者机构：

[Luo, Xingrui; Zheng, Xing] Univ South China, Hunan Prov Cooperat Innovat Ctr Mol Target New Dr, Inst Pharm & Pharmacol, Hengyang 421001, Hunan, Peoples R China.

[Pailla, Santhosh Kumar; Wang, Ruowen; Luo, Xingrui; Gao, Fei] Shanghai Jiao Tong Univ, Renji Hosp, Sch Med, Inst Mol Med,State Key Lab Oncogenes & Related Ge, Shanghai 00240, Peoples R China.

[Wang, Ruowen; Luo, Xingrui] Tsinghua Univ, Dept Biotechnol & Biomed, Yangtze Delta Reg Inst, Jiaxing 314006, Zhejiang, Peoples R China.

通讯机构：

[Zheng, Xing] U

[Wang, Ruowen] S

Univ South China, Hunan Prov Cooperat Innovat Ctr Mol Target New Dr, Inst Pharm & Pharmacol, Hengyang 421001, Hunan, Peoples R China.

Shanghai Jiao Tong Univ, Renji Hosp, Sch Med, Inst Mol Med,State Key Lab Oncogenes & Related Ge, Shanghai 00240, Peoples R China.

语种：

英文

关键词：

Amino acids;Prodrug;SuFEx;Fluorosulfate

期刊：

Tetrahedron

ISSN：

0040-4020

年：

2020

卷：

期：

页码：

130926

DOI：

10.1016/j.tet.2020.130926

基金类别：

NSFCNational Natural Science Foundation of China [NSFC 21877079]; ZJNSFNatural Science Foundation of Zhejiang Province [LY16B020001]

机构署名：

本校为第一且通讯机构

院系归属：

药学与生物科学学院

摘要：

Sulfur (VI) Fluoride Exchange (SuFEx) chemistry is proposed as a new generation of click chemistry with potential in drug discovery and biological study. Herein we report a simple and convenient approach to synthesize amino acid derivatives functionalized with aryl fluorosulfonyl group from a simple building block. Promoted by 1,1'-Carbonyldiimidazole (CDI), methyl protected amino acids and other amines were efficiently functionalized with SO2F by the reaction with 4-((fluorosulfonyl)oxy)benzoic acid giving fluorosulfonylated amides (FSAs) as products. We also demonstrated that FSAs are useful...

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Functionalization of amino acids with aryl fluorosulfate for prodrug construction by SuFEx chemistry

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