Facile and efficient Lewis acid catalyzed synthesis of an asymmetric tetrazine useful for bio-orthogonal click chemistry applications |
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| Authors: | Daniel L Alge Dillon F Donohue Kristi S Anseth |
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| Institution: | 1. University of Colorado at Boulder, Department of Chemical and Biological Engineering, Boulder, CO 80303, USA;2. University of Colorado at Boulder, BioFrontiers Institute, Boulder, CO 80303, USA;3. Howard Hughes Medical Institute, Boulder, CO 80303, USA |
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| Abstract: | Bio-orthogonal tetrazine click reactions have recently attracted significant interest for applications spanning biological imaging, cancer targeting, and biomaterials science. Here, we report a simple and efficient two-step scheme for the synthesis of an asymmetric tetrazine molecule containing a carboxylic acid handle for subsequent macromolecular conjugation. Yields as high as 75% were achieved using as little as 0.005 equiv of nickel triflate catalyst, which is a significant improvement over previous methodologies. |
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| Keywords: | Tetrazine Bio-orthogonal chemistry Click chemistry Lewis acid catalysis |
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