4475. Glutathione

Nomenclature

CAS number: 70-18-8
N-(N-l-γ-Glutamyl-l-cysteinyl)glycine; l-glutathione; glutathione-SH; GSH; Agifutol S (Kyorin); Copren (Fuso); Deltathione (Tobishi); Glutamed (Boehringer, Mann.); Glutasan (Sancarlo); Glutathin (Mochida); Glutathiol; Glutathion (Nichiiko); Glutinal (Sankyo); Isethion (Mect); Neuthion (Senju); Tathiclon (Ohta); Tathion (Yamanouchi); Tationil (Boehringer Biochemia); Triptide.
C10H17N3O6S; mol wt 307.32.
C 39.08%, H 5.58%, N 13.67%, O 31.24%, S 10.43%.

Description and references

The major low mol wt thiol compound of the living plant or animal cell. Isoln from yeast: Hopkins, J. Biol. Chem. 84, 269 (1929). Synthesis: du Vigneaud, Miller, Biochem. Prep. 2, 87 (1952); Goldschmidt et al., Ber. 97, 2434 (1964); Y. Ozawa et al., Bull. Chem. Soc. Jpn. 53, 2592 (1980). Review of early syntheses: Jeschkeit et al., Pharmazie 18, 658 (1963). Review of metabolism: A. Meister, M. E. Anderson, Annu. Rev. Biochem. 52, 711-760 (1983); of metabolic role in antineoplastic chemotherapy: B. A. Arrick, C. F. Nathan, Cancer Res. 44, 4224-4232 (1984). Monographs: S. Colowick et al., Glutathione (Academic Press, New York, 1954); Glutathione, E. M. Crook, Ed., Biochem. Soc. Symposium No. 17, London, 1958 (Cambridge University Press, 1959); Glutathione, L. Flohe et al., Eds. (Academic Press, New York, 1974); Glutathione: Metabolism & Function I. M. Arias, W. B. Jackoby, Eds. (Raven, New York, 1976).

Chemical structure

Properties

Crystals from 50% ethanol, mp 195°. [α]D25 18.9° (c = 4.653). [α]D27 21° (c = 2.74). pK1′ 2.12; pK2′ 3.53; pK3′ 8.66; pK4′ 9.12. Freely sol in water, dil alcohol, liquid ammonia, dimethylformamide.

Derivative

Disulfide.

Nomenclature

CAS number: 27025-41-8
l-γ-Glutamyl-l-cysteinyl-glycine disulfide; N,N′-[dithiobis[1-[(carboxymethyl)carbamoyl]ethylene]]diglutamine; GSSG; oxidized glutathione.
C20H32N6O12S2; mol wt 612.63.
C 39.21%, H 5.26%, N 13.72%, O 31.34%, S 10.47%.

Properties

Crystals, mp 123°. [α]D20 108° (c = 2 in water).