Bulletin of the Chemical Society of Japan p. 2592 - 2593 (1980)
Update date:2022-08-11
Topics:
Ozawa, Yoichi
Tsuji, Toshiaki
Ariyoshi, Yasuo
A convenient synthesis of glutathione (GSH) by the use of minimal protecting groups was investigated.N-Formyl-L-2-amino-4-cyanobutyric acid ethyl ester was condensed with ethyl L-cysteinylglycinate to give (4R)-2-<(3S)-3-ethoxycarbonyl-3-(formylamino)propyl>-4-(ethoxycarbonylmethylcarbamoyl)-2-thiazoline.This compound was saponified in aqueous acetone at -15- -20 deg C and subsequently treated with dilute H2SO4 (pH 4) to yield formylglutathione, whose formyl group was then hydrolyzed with 0.5 M (1M = 1 mol dm-3) H2SO4 to give free GSH.For purification, this was changed to a copper thiolate, which was then decomposed with H2S to afford pure GSH.
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