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. 2023 Nov 8;18(11):2377–2384. doi: 10.1021/acschembio.3c00305

Scheme 1. Proposed Mechanism of PMB Migration during Acidic Deprotection.

Scheme 1

Protonation of the ether results in an attack of the thioether on the benzylic position, instigating PMB migration. Hydrolysis of the sulfonium salt 11 then gives the para-methoxybenzylated thiol of cysteine and free ADPr.