Syntheses of (R) [4-2H2] 2-Amino-3-Butenoic Acid (Vinylglycine) and (R) [4-2H2, 5-2H3] Methionine |
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| Authors: | Avery Rosegay David Taub |
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| Affiliation: | Merck Sharp and Dohme Research Laboratories , P.O. Box 2000, Rahway, N.J., 07065 |
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| Abstract: | Treatment of (R) methionine sulfoxide with NaOD led to exchange of the C-4 methylene and C-5 methyl protons; exchange of the chiral C-2 proton did not occur. Reducation with mercaptoacetic acid gave (R)-[4-2H2, 5-2H3] methionine. The latter was converted into its carbobenzyloxy methyl ester sulfoxide, pyrolysis of which followed by deprotection yielded (R)-[4-2H2] vinylglcine as the hydrochloride. |
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