Fig. 2: 1,2-dithiolane probe design and synthesis. | Nature Communications

Fig. 2: 1,2-dithiolane probe design and synthesis.

From: Cyclic 5-membered disulfides are not selective substrates of thioredoxin reductase, but are opened nonspecifically

Fig. 2

a After opening or reduction of the 1,2-dithiolane in SS50-PQ, thiolate cyclisation releases the precipitating phenol PQ-OH that gives ESIPT-based fluorescence in the solid state. b Synthesis of SS50-PQ: (i) Boc2O, NEt3, dioxane/H2O, r.t., 15 h (96%); then either MsCl, py, DCM followed by KSAc, acetone, 60 °C, 2 h (89%), or HSAc, PPh3, DIAD, THF, 0 °C to r.t., 15 h (88%). (ii) KOH, MeOH, open to air, r.t., 15 h (98%). (iii) MeI, NaH, DMF, 0 °C to r.t., 0.5 h (70%). (iv) PQ-OH, triphosgene, NEt3, DCM, 0 °C to r.t., 1 h; then 6, NEt3, DCM, 0 °C to r.t., 1 h (49%).

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