Organo-Photoredox Catalyzed gem-Difluoroallylation of Glycine and Glycine Residue in Peptides

被引：5

作者：

Lin, Ruofan ^{[1
]}

Shan, Yujie ^{[1
]}

Li, Yan ^{[1
]}

Wei, Xian ^{[1
]}

Zhang, Yue ^{[1
]}

Lin, Yuqian ^{[1
]}

Gao, Yiman ^{[1
]}

Fang, Weiwei ^{[1
]}

Zhang, Jing-Jing ^{[1
]}

Wu, Ting ^{[2
]}

Cai, Lingchao ^{[1
]}

Chen, Zhen ^{[1
]}

机构：

[1] Nanjing Forestry Univ, Coll Chem Engn, Int Innovat Ctr Forest Chem & Mat, Jiangsu Key Lab Biomass Based Green Fuels & Chem,J, Nanjing 210037, Jiangsu, Peoples R China

[2] Chinese Acad Forestry, Inst Chem Ind Forest Prod, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat Fo, Key Lab Biomass Energy & Mat,Natl Forestry & Grass, Nanjing 210042, Jiangsu, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 06期

基金：

中国国家自然科学基金;

关键词：

AMINO-ACIDS; BIOLOGICAL-ACTIVITY; FUNCTIONALIZATION; CYCLOADDITION; DERIVATIVES; GENERATION; ACCESS;

D O I：

10.1021/acs.joc.3c02923

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An organo-photoredox catalyzed gem-difluoroallylation of glycine with alpha-trifluoromethyl alkenes via direct C(sp(3))-H functionalization of glycine and C-F bond activation of alpha-trifluoromethyl alkenes has been described. As a consequence, a broad range of gem-difluoroalkene-containing unnatural amino acids are afforded in moderate to excellent yields. This reaction exhibits multiple merits such as readily available starting materials, broad substrate scope, and mild reaction conditions. The feasibility of this reaction has been highlighted by the late-stage modification of several peptides as well as the improved in vitro antifungal activity of compound 3v toward Valsa mali compared to that with commercial azoxystrobin.

引用

页码：4056 / 4066

页数：11

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