Fig. 4: Secondary transformations of tyrosyl-selenonium salts. | Nature Chemistry

Fig. 4: Secondary transformations of tyrosyl-selenonium salts.

From: A selenoxide for single-atom protein modification of tyrosine residues enabled by water-resistant chalcogen and hydrogen bonding

Fig. 4

a, Transformations of 15. Yields were determined by crude 1H NMR. aNaI, iPrI. bCuBr2, Cu(MeCN)4BF4, KBr. cCuCl2, Cu(MeCN)4BF4, NaCl. dB2(OH)4, NaF, Hantzsch ester, then H2O2. eFeSO4·7H2O, dimethyl 2-(methoxymethylene)malonate, then EDTA-Na2 and NaHCO3. fPd(OAc)2, (4-fluorophenyl)boronic acid. b, Transformations of selenonium bioconjugates. Yields were determined by UV absorption at 214 nm and, if necessary, deconvoluted zero-charge mass spectra. gNaI, iPrI. hCuBr2, Cu(MeCN)4PF6, KBr. iFeSO4·7H2O, dimethyl 2-(methoxymethylene)malonate, then Na-glycine buffer (pH 9.0). jPd(OAc)2, TPPTS, (4-fluorophenyl)boronic acid. kNaI, iPrI. lCuBr2, Cu(MeCN)4PF6, KBr. All reactions were conducted in aqueous buffer containing organic cosolvent 10–40% (v/v). Reactions, except (f) and (j), were irradiated by 390-nm LEDs for 10–20 min. iPr, isopropyl; MeCN, acetonitrile; Ac, acetyl; TPPTS, 3,3′,3′′-phosphanetriyltris(benzenesulfonic acid) trisodium salt.

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