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Oxidation and Phenolysis of Peptide/Protein C-Terminal Hydrazides Afford Salicylaldehyde Ester Surrogates for Chemical Protein Synthesis

  • Shaomin Lin
    Shaomin Lin
    School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China
    More by Shaomin Lin
  • Zeyuan Mo
    Zeyuan Mo
    School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China
    More by Zeyuan Mo
  • Peng Wang
    Peng Wang
    School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China
    More by Peng Wang
  • , and 
  • Chunmao He*
    Chunmao He
    School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China
    *[email protected]
    More by Chunmao He
Cite this: J. Am. Chem. Soc. 2023, 145, 30, 16843–16851
Publication Date (Web):July 20, 2023
https://doi.org/10.1021/jacs.3c05190
Copyright © 2023 American Chemical Society

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    Abstract

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    With the growing popularity of serine/threonine ligation (STL) and cysteine/penicillamine ligation (CPL) in chemical protein synthesis, facile and general approaches for the preparation of peptide salicylaldehyde (SAL) esters are urgently needed, especially those viable for obtaining expressed protein SAL esters. Herein, we report the access of SAL ester surrogates from peptide hydrazides (obtained either synthetically or recombinantly) via nitrite oxidation and phenolysis by 3-(1,3-dithian-2-yl)-4-hydroxybenzoic acid (SAL(−COOH)PDT). The resulting peptide SAL(−COOH)PDT esters can be activated to afford the reactive peptide SAL(−COOH) esters for subsequent STL/CPL. While being operationally simple for both synthetic peptides and expressed proteins, the current strategy facilitates convergent protein synthesis and combined application of STL with NCL. The generality of the strategy is showcased by the N-terminal ubiquitination of the growth arrest and DNA damage-inducible protein (Gadd45a), the efficient synthesis of ubiquitin-like protein 5 (UBL-5) via a combined N-to-C NCL-STL strategy, and the C-to-N semisynthesis of a myoglobin (Mb) variant.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.3c05190.

    • Experimental details, Tables S1–S3, and Figures S1–S32 (PDF)

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