Kondrat鈥檈va Ligation: Diels鈥揂lder-Based Irreversible Reaction for Bioconjugation
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- 作者：Laurie-Anne Jouanno ; Arnaud Chevalier ; Nawal Sekkat ; Nicolas Perzo ; H茅l猫ne Castel ; Anthony Romieu ; Norbert Lange ; Cyrille Sabot ; Pierre-Yves Renard
- 刊名：Journal of Organic Chemistry
- 出版年：2014
- 出版时间：November 7, 2014
- 年：2014
- 卷：79
- 期：21
- 页码：10353-10366
- 全文大小：705K
- ISSN：1520-6904
文摘
Diversification of existing chemoselective ligations is required to efficiently access complex and well-defined biomolecular assemblies with unique and valuable properties. The development and bioconjugation applications of a novel Diels鈥揂lder-based irreversible site-specific ligation are reported. The strategy is based on a Kondrat鈥檈va cycloaddition between bioinert and readily functionalizable 5-alkoxyoxazoles and maleimides that readily react together under mild and easily tunable reaction conditions to afford a fully stable pyridine scaffold. The potential of this novel bioconjugation is demonstrated through the preparation of fluorescent conjugates of biomolecules and a novel F枚rster resonance energy transfer (FRET)-based probe suitable for the in vivo detection and imaging of urokinase-like plasminogen activator (uPA), which is a key protease involved in cancer invasion and metastasis.