L-aspartyl-L-phenylglycine esters of lower alkanols

Details L-aspartyl-L-phenylglycine esters of lower alkanols L-aspartyl-L-phenylglycine esters of lower alkanols

1969-09-02

1976-08-03

Gotts, Lewis

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

426548, C07C10352, A23L 122

Patent

active

039728609

ABSTRACT:
L-aspartyl-L-phenylglycine esters, e.g., L-aspartyl-L-phenylglycine methyl ester, are new compounds useful as sweeteners for various foods, beverages and compositions intended to be tasted, e.g., chewing gums, dentifrices, mouth washes. Such compounds can be made by reaction of a corresponding amide, such as asparagine, with an amino blocking agent, e.g., carbobenzoxy chloride, whereby a reaction with the amino group of the asparagine produces the corresponding carbobenzoxyamide, following which the amide is reacted with the methyl or other suitable lower alkyl ester of an amino acid, e.g., phenylglycine, to produce the corresponding peptide by reaction of the free carboxylic and amino groups, and subsequently, the carbobenzoxy group is removed by hydrogenolysis in the presence of a catalyst and the terminal amide of the peptide is converted to the corresponding acid by hydrolysis.

REFERENCES:
patent: 3264280 (1966-08-01), Hofmann et al.
patent: 3299035 (1967-01-01), Boissonnas et al.
patent: 3450687 (1969-06-01), Hobbs
patent: 3475403 (1969-10-01), Mazur et al.
patent: 3492131 (1970-01-01), Schlatter
Bergmann et al., Chem. Ber. 65, 1198 (1932).
Mazur et al., J. Am. Chem. Soc. 91, 2684-2691 (1969).
Anderson et al., Acta Chim. Akad. Sci. Hung. 44, 187-195 (1965).
Bergmann et al., Chem. Ber. 65, 1196-1197 (1932).
Zaoral et al., Coll. Czech. Chem. Commun. 24, 2010 (1959).

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