Chemistry of carbon compounds – Dipeptides – e.g. – aspartame – anserine – carnosine – etc. – Aspartylphenylalanone esters and cyclohexylalanine esters
Patent
1984-12-28
1986-07-15
Schofer, Joseph L.
Chemistry of carbon compounds
Dipeptides, e.g., aspartame, anserine, carnosine, etc.
Aspartylphenylalanone esters and cyclohexylalanine esters
525 5411, 530334, C07K 0000
Patent
active
046005323
ABSTRACT:
Reaction of a ketoxime-derivatized resin with a strong acid salt of aspartic anhydride or glutamic anhydride yields a novel aspartyl or glutamyl ketoxime ester-derivatized resin, wherein the aspartyl or glutamyl groups are esterified predominantly at the .alpha.-carboxyl group and wherein the aspartyl or glutamyl groups are not covalently protected at the amino group or the carboxyl group that is not esterified. Aminolysis in the presence of a weak acid of the novel aspartyl or glutamyl ketoxime ester-derivatized resin, wherein the aspartyl or glutamyl groups remain as the strong acid salt, with a salt of an amino acid with a base or an amino acid ester yields the corresponding dipeptide or dipeptide ester. After aminolysis, the ketoxime-derivatized resin can be reused. An advantageous solid-phase method is thus provided for making .alpha.-L-aspartyl dipeptide ester sweeteners, including aspartame, and the immunopotentiating dipeptide, .alpha.-L-glutamyl-L-asparagine.
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Kaiser Emil T.
Musso Gary F.
Lipman Bernard
Schofer Joseph L.
The Salk Institute Biotechnology Industrial Associates, Inc.
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