Process and composition for amino-terminal, .alpha.-aspartyl and .alpha.-glutamyl dipeptide esters
US4731412A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Apr 14, 1986 |
| Grant date | Mar 15, 1988 |
| Priority date | — |
| Expiry date | Apr 14, 2006 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07K5/06104
- WIPO fieldBiotechnology
- WIPO sectorChemistry
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 aminoylsis, 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.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.