Bioorthogonal chemistries can be used to visualize and identify diverse classes of biomolecules in complex environments.  Despite the tremendous success of these reactions in revealing new facets of cell and organismal biology, significant limitations remain: (1) many of the most common reactions are incompatible with one another, limiting their utility for studies of multiple biomolecules in tandem, and (2) many bioorthogonal reagents are too large for tagging native biomolecules in live cells.  Thus, identifying new transformations that are not only suitable for use in vivo�but that also work well in tandem�remain important goals in chemical biology.  We have developed new classes of bioorthogonal reactions using functionalized cyclopropenes.  Cyclopropenes are attractive motifs for use in cells owing to their small size, biocompatibility, and diverse manifolds of reactivity.  To date, we have identified three classes of small, strained cyclopropenes that exhibit unique reactivities and can be used concurrently for multi-component bioorthogonal labeling.  Our progress in these areas will be discussed.

Expanding the bioorthogonal toolkit

248th National Meeting (2014)

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