Croatica Chemica Acta, Vol. 31 No. 2, 1959.
Original scientific paper
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
Abstract
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.
Keywords
Hrčak ID:
245257
URI
Publication date:
24.9.1959.
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