Synfacts 2021; 17(01): 0091
DOI: 10.1055/s-0040-1719253
Chemistry in Medicine and Biology

Teaching Old Clicks New Tricks

Dirk Trauner
Alexander J. E. Novak
Hu Y, Roberts JM, Kilgore HR, Lani AS. M, Raines RT, *, Schomaker JM. * Massachusetts Institute of Technology, Cambridge and University of Wisconsin–Madison, USA
Triple, Mutually Orthogonal Bioorthogonal Pairs through the Design of Electronically Activated Sulfamate-Containing Cycloalkynes.

J. Am. Chem. Soc. 2020;
142: 18826-18835
DOI: 10.1021/jacs.0c06725.


The introduction of bioorthogonal reactions has enabled tremendous advances in chemical biology. The authors designed two new, mutually orthogonal pairs by electronic tuning of S-, N-, and O-containing cyclooctynes (SNO-OCTs). The reported system should prove to be a useful tool for future in cellulo investigations.



Using computational and experimental studies, the authors were able to design cyclooctynes with orthogonal reactivities. By including a previously reported boronic acid/hydrazine pair, the authors were able to obtain a triple ligation system and demonstrated its utility through protein and cellular labeling assays.


Publication History

Publication Date:
16 December 2020 (online)

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