Fluorogenic Behaviour of the Hetero-Diels-Alder Ligation of 5-Alkoxyoxazoles with Maleimides and their Applications

被引：7

作者：

Renault, Kevin ^{[1
]}

Jouanno, Laurie-Anne ^{[2
]}

Lizzul-Jurse, Antoine ^{[1
]}

Renard, Pierre-Yves ^{[1
]}

Sabot, Cyrille ^{[1
]}

机构：

[1] Normandie Univ, CNRS, UNIROUEN, INSA Rouen COBRA UMR 6014, F-76000 Rouen, France

[2] Univ Ottawa, Dept Chem & Biomol Sci, 10 Marie Curie, Ottawa, ON K1N 6N5, Canada

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 51期

关键词：

azaphthalimide; Diels-Alder; fluorescence spectroscopy; ligation; oxazole; CLICK CHEMISTRY; FLUORESCENT-PROBE; CYCLOADDITION; DESIGN; STRATEGIES; PEPTIDES; ALDEHYDE; ALKYNES;

D O I：

10.1002/chem.201603617

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Fluorogenic reactions are largely underrepresented in the toolbox of chemoselective ligations despite their tremendous potential, particularly in chemical biology and biochemistry. In this respect, we have investigated in full detail the fluorescence behaviour of the azaphthalamide, a scaffold which is generated through a hetero-Diels-Alder reaction of 5-alkoxyoxazole and maleimide derivatives under mild conditions that are compatible with, among others, peptide chemistry. The scope and limitations of such a fluorogenic labelling strategy were examined through four distinct applications, which target enzymatic activities or bioorthogonal reactions.

引用

页码：18522 / 18531

页数：10

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