Efficient and Selective Syntheses of S-Acyl and N-Acyl Glutathiones

Abstract

Selective syntheses of S-acyl glutathiones are achieved in 79–98% yields using 1-acyl-1H-benzotriazoles in the presence of potassium bicarbonate in aqueous methanol at 20 °C. N-Acylation of S-(p-nitrobenzoyl) glutathione with 1-acyl-1H-benzotriazoles followed by deprotection of the p-nitrobenzoyl groups under mild conditions gave 63–78% yields of N-acyl glutathiones. These meth-odologies should be useful for the S-acylation and N-acylation of peptides and glycopeptides.