Issue 40, 2023

Resin-supported cyclic telluride as a heterogeneous promoter of disulfide formation under solid–liquid biphasic conditions

Abstract

The oxidative crosslinking of thiols via a disulfide (SS) bond is a fundamental chemical reaction in the industrial production of protein- and peptide-based formulations. In this study, we developed a new heterogeneous catalyst/mediator, polystyrene-resin-immobilized cyclic telluride [(S)-tetrahydrotellurophen-3-amine] (RSTe), which significantly promotes the oxidation of thiols to disulfides (SS formation). Under solid–liquid biphasic reaction conditions, RSTe exhibited glutathione-peroxidase-like activity in the oxidative SS formation of 15 organic solvent- and water-soluble thiols using a peroxide (H2O2 or tBuOOH) as an oxidant. Notably, all reactions were completed within 90 min, and RSTe and the peroxide could be removed by filtration and concentration, respectively, thereby affording the target disulfides in sufficient yield and purity without further purification. This reaction system could also be utilized for SS formation in cysteine-containing polypeptide chains, suggesting the potential application of RSTe in oxidative folding, which is an essential process in the production of bioactive proteins.

Graphical abstract: Resin-supported cyclic telluride as a heterogeneous promoter of disulfide formation under solid–liquid biphasic conditions

Supplementary files

Article information

Article type
Paper
Submitted
08 jun. 2023
Accepted
25 ago. 2023
First published
28 ago. 2023

New J. Chem., 2023,47, 18537-18546

Resin-supported cyclic telluride as a heterogeneous promoter of disulfide formation under solid–liquid biphasic conditions

Y. Nishizawa, Y. Satoh, O. Kanie and K. Arai, New J. Chem., 2023, 47, 18537 DOI: 10.1039/D3NJ02646A

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