Process and composition for amino-terminal, .alpha.-aspartyl and

Details Process and composition for amino-terminal, .alpha.-aspartyl and Process and composition for amino-terminal, .alpha.-aspartyl and

1986-04-14

1988-03-15

Smith, Edward J.

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

5253282, 530334, C08F 832

Patent

active

047314125

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.

REFERENCES:
patent: 3462460 (1969-08-01), Kollonitsch
patent: 3786039 (1974-01-01), Ariyoshi et al.
patent: 3798206 (1974-03-01), Uchiyama et al.
patent: 3833553 (1974-09-01), Ariyoshi et al.
patent: 3920626 (1975-11-01), Ariyoshi et al.
patent: 3962207 (1976-06-01), Uchiyama et al.
patent: 3985715 (1976-10-01), Gray
patent: 4089821 (1978-05-01), Enkoji et al.
patent: 4171412 (1979-10-01), Coupek et al.
patent: 4242238 (1980-12-01), Colescott et al.
patent: 4301045 (1981-11-01), Kaiser et al.
patent: 4426324 (1984-01-01), Meienhofer
patent: 4507230 (1985-03-01), Tom et al.
Fujino and Nishimura, "The Use of Simple Ketoximes in Peptide Synthesis," em. Pharm. Bull. (Japan) 17, 1937-1941 (1969).
Ariyoshi et al., "The Synthesis of a Sweet Peptide . . . Without the Use of Protecting Groups," Bull. Chem. Soc. (Japan) 46, 1893-1895 (1973).
Ariyoshi et al., "The Synthesis of Salts of L. Aspartic Anhydride with Alkyl-Sulfuric Acid and Their Use in the Preparation of Aspartylphenylalanie Methyl Ester," Bull. Chem. Soc. (Japan) 46, 2611-2612 (1973).
DeGrado and Kaiser, "Polymer-Bound Oxime Esters As Supports for Solid-Phase Peptide Synthesis, Preparation of Protected Peptide Fragments," J. Org. Chem. 45, 1295-1300 (1980).
Vinick and Jung, "A Superior Synthesis of Aspartame," Tetrahedro Lett. 23, 1315-1318 (1982).
DeGrado and Kaiser, "Solid-Phase Synthesis of Protected Peptides on a Polymer-Bound Oxime . . . , " J. Org. Chem. 47, 3258-3261 (1982).
Nakagawa and Kaiser, "Synthesis of Protected Peptide Segments and Their Assembly on a Polymer-Bound Oxime," J. Org. Chem. 48, 678-685 (1983).
Hayashi and Shimizu, "Reactivity of Aromatic o-Hydroxy Oximes II," Bull. Chem. Soc. (Japan) 56, 3197-3198 (1983).

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