Bioorthogonal chemistries enable the investigation of diverse biomolecules in cellular environments.  While versatile, many of the most popular ligations cannot be used in tandem owing to cross-reactivities.  Multi-component labeling studies would benefit from the development of mechanistically distinct transformations. Toward this end, we have developed a novel bioorthogonal reaction of phosphines and cyclopropeniminium ions.  These latter reagents are the nitrogenous equivalent of cyclopropenones, a recently reported bioorthogonal motifs. A panel of cyclopropeniminium ions was synthesized, and reagent stabilities in aqueous and physiological environments were analyzed.  The probes were incubated with various phosphines and reaction rates were measured.  Unique covalent adducts were formed upon nucleophile-tethered phosphine addition to the cyclopropeniminium scaffold. Collectively, these data suggest the cyclopropeniminium-phosphine ligation is mutually orthogonal to a variety of well-known bioorthogonal reactions and will be a useful addition to the bioorthogonal toolkit for multi-component labeling.<br/>

A bioorthogonal ligation of cyclopropeniminium cations and phosphines

256th National Meeting (2018)

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