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. 2025 May 8;86(3):e70095. doi: 10.1002/ddr.70095

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© 2025 The Author(s). Drug Development Research published by Wiley Periodicals LLC.

This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

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SCHEME 3 — Summary of previous studies evaluating the nonenzymatic reactivities of acrylamides, vinyl sulfonamides, and vinyl sulfones (Hillebrand et al. 2024). Arrows show the increase in reactivity for pairs of molecules examined under identical conditions, with the enhanced reactivity in parentheses calculated from the related rate enhancements. The value of 580‐fold (Ábrányi ‐Balogh et al. 2018) refers to glutathione (GSH) in phosphate buffered saline (PBS). The value of 440‐fold (Kathman et al. 2014) refers to Ac‐Cys‐OMe in 2:1 PBS:DMSO at pD 8.0. The values of twofold and 110‐fold (Gehringer and Laufer 2019) refer to GSH in phosphate buffer at pH 7.4. The values of sevenfold and 65‐fold (Flanagan et al. 2014) refer to GSH in phosphate at pH 7.4. A value of ninefold for terminal vinyl sulfone versus acrylamide (Martin et al. 2019) refers to Boc‐Cys‐OMe in PBS. The value of 120‐fold (Reddick et al. 2003) refers to (phenylethyl)thiol in methanol with triethylamine.