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The Resolution of B-Amino-1-methylsulphinyl-butyric Acid(B-Methionine Sulphoxide) into Four Optical Isomers

D. Keglević ; Tracer Laboratory, Institute »Ruder Boskovic«, Zagreb, Croatia, Yugoslavia
B. Ladešić ; Tracer Laboratory, Institute »Ruder Boskovic«, Zagreb, Croatia, Yugoslavia


Puni tekst: engleski pdf 11.571 Kb

str. 57-66

preuzimanja: 107

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Sažetak

The preparation of four optical isomers of B-amino-y-methylsulphinyl-butyric acid (B-methionine sulphoxide) is described. S-Benzyl-DL-B-homocysteine was resolved via its brucine salt intothe optically active forms (Ila and lib) which were then converted to L- resp. D-B-methionine (Illa and IIIb). By desulphurization with Raney-Nickel to the corresponding B-amino acids (IVa and IVb), the optical purity of Illa and IIIb was confirmed. Oxidation of IIIa and IIIb with hydrogen peroxide yielded the diastereoisomeric mixtures of L- resp. D-B-methionine sulphoxides; they were resolved into four optical isomers through picrates resp . through fractional crystallization. The rotation values of pure isomers as well as percentages of isomers occurring in the diastereoisomeric mixtures are given.

Ključne riječi

Hrčak ID:

245257

URI

https://hrcak.srce.hr/245257

Datum izdavanja:

24.9.1959.

Posjeta: 285 *