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. Author manuscript; available in PMC: 2021 May 6.
Published in final edited form as: J Am Chem Soc. 2020 Apr 24;142(18):8270–8280. doi: 10.1021/jacs.0c00648

Figure 2. Tuning reactivity of the sulfur electrophile.

Figure 2.

SuTEx fragments were incubated with p-cresol in the presence of tetramethylguanidine (TMG, 1.1 equivalents) base and time-dependent covalent reaction monitored by the reduction of respective fragment starting material. Modifications to the adduct group (AG; A) and triazole leaving group (LG; B) could alter solution reactivity of SuTEx fragments. The calculated half-life of individual SuTEx fragments are shown in parentheses. The half-lives for all SuTEx fragments tested are listed in Table S1. Formation of the p-cresol adduct was confirmed by retention time that matched synthetic standards for respective reaction products (see Supporting Information for details of HPLC methods and data). Data shown are representative of n = 3 independent experiments.