Amination of Isonitriles in Water: Urea Synthesis under Biocompatible Conditions

Bioorthogonal reactions have been widely used to track biomolecules in living systems. Due to stringent requirements of physiological conditions, enriching the toolkit of bioorthogonal reactions remains the most important and challenging issue. Herein, the biocompatible ligation of isonitriles and a...

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Bibliographic Details
Published in:European journal of organic chemistry 2023-10, Vol.26 (37)
Main Authors: Zhang, Qi, Wang, Xueting, Chen, Shi‐Wu, Tang, Meng, Zhang, Qian, Xia, Yiwen
Format: Article
Language:English
Subjects:
Alkynes
Amines
Aqueous solutions
Biocompatibility
Biomolecules
Cycloaddition
Substrates
Ureas
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Summary:Bioorthogonal reactions have been widely used to track biomolecules in living systems. Due to stringent requirements of physiological conditions, enriching the toolkit of bioorthogonal reactions remains the most important and challenging issue. Herein, the biocompatible ligation of isonitriles and amines to ureas in neutral aqueous medium was developed for the first time. The ligation showed benign nature of biocompatibility, broad substrate scope, and specific chemoselectivity. Meanwhile, urea as a natural linkage, its derivatives played an important role in medicinal chemistry. The second‐order reaction rate constant ( k 2 ) was determined, which was higher or comparable to that of Staudinger ligation and strain‐promoted azide‐alkyne cycloaddition (SPAAC). Direct labeling of Ac 4 GlcN has been achieved in Hep G2 cells.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202300779