S-allylmercaptoglutathione was synthesized after a method modified from Miron et al. [12 (link)]. GSH (400 mg dissolved in 5 mL distilled H2O) were added dropwise with stirring to 130 mg allicin dissolved in 2 mL 50% (v/v) methanol and stirred for a further 2 h at room temperature. The white precipitate (yield 450 mg) was washed repeatedly with dichloromethane and the product gave a single peak which eluted from HPLC at 5.8 min (conditions as in [18 (link)]).
The identity of the product was confirmed by electrospray ionization mass spectrometry (ESI-MS). Measurements were carried out on a Thermo Fisher Scientific Orbitrap XL (in high resolution mode using methanol/water (50%/50%) with 0.1 mM acetic acid.
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