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. Author manuscript; available in PMC: 2018 Jul 23.
Published in final edited form as: ACS Chem Biol. 2018 Jul 6;13(7):1810–1823. doi: 10.1021/acschembio.8b00371

Scheme 2.

Scheme 2

Representative examples of two predominant mechanisms of activation in auto-immolative linkers: (A) elimination and (B) acyl transfer. Enzymatic catalysis releases a masking group (R1–CO2H). Then, elimination to form a quinone methide (A)27 or acyl transfer driven the action of a trimethyl lock (B)25 rapidly releases a fluorophore (R2–OH or R2–NH2).