One-Pot Synthesis of Glutathione Trisulfide from Oxidized Glutathione.
J Org Chem
; 89(15): 10946-10952, 2024 Aug 02.
Article
em En
| MEDLINE
| ID: mdl-39041585
ABSTRACT
The excellent medicinal efficacy of glutathione trisulfide, an endogenous compound consisting of sulfane sulfur and two molecules of reduced glutathione, has been reported in recent years. However, no efficient procedure for the synthesis of trisulfide is yet available. Herein, we investigated the optimal conditions for the oxidation reaction of oxidized glutathione to thiosulfinate and its subsequent trisulfidation reaction using commercially available materials. The optimized one-pot reactions enabled the isolation of glutathione trisulfide dihydrate by crystallization on a 20 g scale in high yield (up to 74% for the two steps, >95% purity). Liquid chromatography-mass spectrometry/MS (LC-MS/MS) measurements using Na234S as a sulfur source revealed that 34S was inserted only into the center of the trisulfide with high selectivity (>99% enrichment) during the reaction. The reaction mechanism indicated that disulfide bonds were cleaved by the reaction of thiosulfinate and a sulfur source, followed by trisulfide bond-formation via the dehydration condensation of sulfenic acid and persulfide.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Glutationa
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2024
Tipo de documento:
Article