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. 2012 Dec 1;17(11):1590–1609. doi: 10.1089/ars.2011.4406

FIG. 4.

FIG. 4.

The first step of Michael addition. C-3 has electron density moved toward O atom of OH on C-4 due to inductive effect (Inline graphic). At the same time, resonance between the double bond between C-3 and C-2 and the aldehyde dumps electron density away from C-3. The net effect is a partially positive C-3 that becomes a target for electrophilic reaction of lone pair of electrons on the S atom of cysteine.