Acid-catalyzed Esterification and Biotin/Fluorescent Labeling of Glutathione Polysulfides Based on Stability under Heating and pH Change

Abstract

Glutathione polysulfides GSSSG and GSSSSG are stable in water up to 80 °C and below pH 9. Their carboxyl groups can be efficiently esterified with TMSCl in alcohols, reacting first at glycine, then glutamic acid. The resulting 3-butyne-1-yl esters allow Cu-catalyzed labeling (e.g., biotin, fluorophore) and can be hydrolyzed by esterases.

Supplementary files

Article information

Article type
Communication
Submitted
10 Dec 2025
Accepted
31 Dec 2025
First published
03 Jan 2026

Chem. Commun., 2026, Accepted Manuscript

Acid-catalyzed Esterification and Biotin/Fluorescent Labeling of Glutathione Polysulfides Based on Stability under Heating and pH Change

M. Yazaki, Y. Zhang, L. Zhou, R. Morise, T. Akaike and M. Arisawa, Chem. Commun., 2026, Accepted Manuscript , DOI: 10.1039/D5CC07029E

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