Fig. 1: Selenoxide-based electrophilic aromatic substitution. | Nature Chemistry

Fig. 1: Selenoxide-based electrophilic aromatic substitution.

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

Fig. 1

a, Thianthrenation: although versatile and highly selective, functionalization with the water-sensitive TT-OTFA+ can only proceed under anhydrous conditions. b, This work: positional-selective, versatile single-atom protein modification with a selenium-based electrophile. The more basic selenoxide group, and the combination of the water-resistant, intramolecular chalcogen and hydrogen bonding, leads to the water-stable electrophile 1H+, thus enabling modification in water. Ac, acetyl; TT, thianthrene; TFA, trifluoroacetyl group; TM, transition metal; X, functional group (for example, halogenyl, hydroxyl).

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