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. Author manuscript; available in PMC: 2018 Apr 13.
Published in final edited form as: J Am Chem Soc. 2017 Apr 10;139(15):5588–5595. doi: 10.1021/jacs.7b01791

Figure 1.

Figure 1

Targeting the cysteine thiol (Cys-SH) with covalent inhibitors. (a) FDA-approved Afatinib forms a covalent adduct with EGFR 797Cys-SH via Michael addition. (b) Oxidation of Cys-SH generates cysteine sulfenic acid (Cys-SOH). (c) Covalent inhibitors with electrophilic warheads (such as the Michael acceptor highlighted in gray) undergo facile reaction with Cys-SH but not with Cys-SOH under physiological conditions.