We report here a deep mechanistic study of the "click" -quinone methide (QM) cycloaddition between -quinolinone quinone methide (QQM) and thio-vinyl ether (TV), named as TQ-ligation. DFT calculations revealed the unexpected fact that dehydration of QQM precursors is the rate-determining step of this transformation, and two highly reactive QQM precursors were predicted. Guided by the calculations, a new "click" QM cycloaddition which shows significantly improved kinetics and remarkable efficiency on protein labeling was developed.
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| http://dx.doi.org/10.1021/acs.orglett.0c00578 | DOI Listing |
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