Development of Water‐Soluble 3‐Nitro‐2‐Pyridinesulfenate for Disulfide Bond Formation of Peptide Under Aqueous Conditions
Year: 2025
Type: article
Abstract: 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.
Source: Chemistry - A European Journal
Authors: Akihiro Taguchi, Megumi Sakata, Ryusei Yamamoto, Hayate Shida, Saeka Kuraishi, Sho Konno, Kentaro Takayama, Atsuhiko Taniguchi, Yoshio Hayashi
Language: English
Subfield: Molecular Biology
Domain: Life Sciences
Open Access status: hybrid
Estimated APC paid: $4,640
Awards: Synthesis and Medicinal Chemical Development of Mid-Sized Peptide Conjugate Based on the Chemistry of Solid-Phase Disulfide Ligation, Development of innovative drug discovery based on SARS-CoV-2 3CL protease inhibitor YH-53, Development of thiol-selective disulfide forming reagent for the application to peptide chemistry
OpenAlex ID: W4409733801