Ahn and Kee designed thioacetylene probes that exploit sulfur-mediated stabilization of a vinyl radical intermediate. DFT (M06-2X/6-31++G(d,p)) predicts a 3.24 kcal/mol lower activation barrier than a conventional alkyne (~200-fold rate gain at room temperature), with radical density delocalized onto sulfur at TS1 .
In vitro: 85% conversion for thioacetylene 1 vs 32% for alkyne 2 at 5 min; TEMPO inhibition, UV/DPAP/cysteine dependence, and a DBU control (<10% at 30 min) support radical selectivity over thiolate addition . BSA labeling localized to the sole free cysteine Cys34. Live E. coli profiling with DTB-thioacetylene 5 (3 replicates) yielded 157 reproducible sites; 116/127 Class I sites (91.3%) were cysteine, including canonical radical sites NrdA Cys439 and PflB Gly734. NrdA labeling required its radical donor NrdB and was abolished by hydroxyurea β the strongest mechanistic validation .
Strengths: rare mechanism-first design (computation β kinetics β live-cell MS); multiple orthogonal controls (TEMPO, hydroxyurea, H2O2/Co(II) dependence, catalase); data deposited (PRIDE PXD070878); no declared conflicts . Weaknesses: only E. coli profiled; most Class I sites are functionally annotated but not individually validated β the authors themselves caution that annotations describe functional categories, not direct evidence of thiyl radicals at each site; non-cysteine assignments (including PflB Gly734) could reflect MS mislocalization or off-target reactivity; no false-discovery or enrichment-efficiency statistics reported. Prior spin-trap methods (DMPO, SH2β² traps) suffered thiolate/ROS cross-reactivity , and thiyl radical redox chemistry is well characterized in vitro (E_m(GSβ’/GSH) = 0.92 Β± 0.03 V at pH 7.4) , making a live-cell trapping tool genuinely novel. What would falsify the selectivity claim: an alkyne-control probe showing equivalent cysteine labeling, or scavenger-insensitive labeling. Whether the "thiylome" extends to mammalian cells and whether the Map Cys169 Fenton-like mechanism generalizes to other metalloproteins remain open β these are precisely what follow-up studies should test.
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