Development of Water‐Soluble 3‐Nitro‐2‐Pyridinesulfenate for Disulfide Bond Formation of Peptide Under Aqueous Conditions

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Establishing an efficient method for the synthesis of disulfide bonds in peptides is an important challenge for the further development of several research fields, including peptide-based medicinal chemistry and biochemistry. Herein, we report the development of a novel highly water-soluble 3-nitro-2-pyridine (Npy) sulfenate that efficiently forms intramolecular disulfide bonds in reduced peptides. Moreover, Npy-sulfenate formed a disulfide bond in a thiol-containing peptide prepared by thiol-additive-free native chemical ligation (NCL), as demonstrated by the one-pot synthesis of adrenomedullin, which contains 52 amino acid residues. This study provides a new one-pot synthetic methodology for preparing mid-sized cyclic disulfide peptides via sulfenate-mediated oxidation.