[Zurück]

W. Kuba, M. Wilkovitsch, J. Carlson, H. Mikula:
"Tetrazine-Based Cycloadditions in Click Chemistry";
in: "Science of Synthesis - Click Chemistry", 4; Thieme, Stuttgart, 2021, ISBN: 9783132435575, 64 S.

The spontaneous cycloaddition of tetrazines with a number of different dienophiles has become a powerful tool in chemical biology, in particular for the biocompatible conjugation and modification of (bio)molecules. The exceptional reaction kinetics made these bioorthogonal ligations the methods of choice for time-critical processes at very low concentrations, facilitating controlled molecular transformations in complex environments and even in vivo. The emerging concept of bond-cleavage reactions triggered by tetrazine-based cycloadditions enabled the design of diagnostic and therapeutic strategies. The tetrazine-triggered activation of prodrugs represents the first bioorthogonal reaction performed in humans, marking the beginning of the era of clinical translation of bioorthogonal chemistry. This chapter provides an overview of the synthesis and reactivity of tetrazines, their cycloadditions with various dienophiles, and transformations triggered by these reactions, focusing on reaction mechanisms, kinetics and efficiency, and selected applications.

Click Chemistry

http://dx.doi.org/10.1055/sos-SD-235-00300