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Bioorthogonal Cycloadditions with Sub-Millisecond Intermediates
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DOI：10.1002/anie.201710262.png)
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Abstract
En 中文
Tetrazine- and sydnone-based click reactions have emerged as important bioconjugation strategies with fast kinetics and N-2 or CO2 as the only byproduct. Mechanistic studies of these reactions have focused on the initial rate-determining cycloaddition steps. The subsequent N-2 or CO2 release from the bicyclic intermediates has been approached mainly through computational studies, which have predicted lifetimes of femtoseconds. In the present study, bioorthogonal cycloadditions involving N-2 or CO2 extrusion have been examined experimentally at the single-molecule level by using a protein nanoreactor. At the resolution of this approach, the reactions appeared to occur in a single step, which places an upper limit on the lifetimes of the intermediates of about 80 mu s, which is consistent with the computational work.
Keywords:
bioorthogonal chemistry
click chemistry
cycloaddition
single-molecule studies
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