Method of preparing gamma-L-glutamyl taurine

Details Method of preparing gamma-L-glutamyl taurine Method of preparing gamma-L-glutamyl taurine

1977-07-11

1982-04-13

Siegel, Alan

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07C14302

Patent

active

043247431

ABSTRACT:
A process for preparing gamma-L-glutamyl-taurine, which has been found to be effective therapeutically through the control of vitamin A metabolism, which comprises reacting carbobenzyloxy-L-glutaminic acid-.alpha.-benzyl ester with triethylamine and isobutylchloroformate and then treating the reaction mixture with cystamine dihydrochloride to recover N,N'-bis-(N-carbobenzyloxy-gamma-[.alpha.-benzyl]-L-glutamyl)-cystamine. The latter is reacted with hydrogen peroxide in glacial acetic acid to produce carbobenzyloxy-gamma-(.alpha.-benzyl)-L-glutamyl taurine. The latter compound is treated with hydrogen bromide in glacial acetic acid to recover the gamma-(.alpha.-benzyl)-L-glutamyl taurine and this compound is treated with potassium hydroxide solution to yield the gamma-L-glutamyl taurine.

REFERENCES:
patent: 3384662 (1968-05-01), Hollinger et al.
patent: 3645996 (1972-02-01), Southard
patent: 3706790 (1972-12-01), Sprague et al.
patent: 3763232 (1973-10-01), Kaiser et al.
patent: 3852338 (1974-12-01), Kaiser et al.
patent: 3943173 (1976-03-01), Colella et al.
patent: 3954783 (1976-05-01), Scherberich
Boissonnas, "Advances in Org. Chem.", vol. 3, pp. 159-190, (1963).

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