Scheme 1: Scope of the C-terminal amino acids for the VTANCL strategya. | Communications Chemistry

Scheme 1: Scope of the C-terminal amino acids for the VTANCL strategya.

From: Rapid vinyl thianthrenium tetrafluoroborate-promoted thioacid-based native chemical ligation and its applications in chemical protein synthesis

Scheme 1: Scope of the C-terminal amino acids for the VTANCL strategya.The alternative text for this image may have been generated using AI.

a Reaction scheme of ligation. b Results of various C-terminal amino acid substructs. aThe concentration of 1a, 1e-1u was 2.0 mM in the first VTT-promoted thioesterification step, and all 3a was 1.5 mM (1.5 e.q) in the second ligation step; Yields presented were calculated through the application of the internal standard method, whereas isolated yields obtained following RP-HPLC purification by weight over two steps are provided in parentheses; bConditions: pH 2.0 and VTT (1.5 eq.) during the first VTT-promoted thioesterification step; cConditions: pH 4.0 and VTT (1.5 eq.) during the first VTT-promoted thioesterification step; dConditions: VTT (1.5 eq.) during the first VTT-promoted thioesterification step; eConditions: pH 8.5 during the second ligation step; fConditions: VTT (1.4 eq.) during the first VTT-promoted thioesterification step, and pH 8.5 during the second ligation step; For more details, refer to the supplementary information.

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