57623-09-3Relevant academic research and scientific papers
Probing the Scope of the Amidine–1,2,3-triazine Cycloaddition as a Prospective Click Ligation Method
Siegl, Sebastian J.,Vrabel, Milan
, p. 5081 - 5085 (2018)
Despite recent achievements in the development of chemical reactions enabling selective modification of complex biomolecules, the demand for fast and efficient methodologies that allow the attachment of various functional groups to these systems is the subject of intense research. Here, we report on the study of the amidine–1,2,3-triazine cycloaddition reaction, which has the potential to address many of the challenges associated with the development of such chemistry. We describe an optimized protocol leading to the in situ formation of free amidine bases, which directly react in the cycloaddition reaction with 1,2,3-triazines. Our kinetic studies reveal the structural features determining the reaction rates. Finally, we show that the amidine–1,2,3-triazine cycloaddition is extraordinarily selective and orthogonal to other popular ligation reactions. The pros and cons of the methodology are presented.
