Syntheses of (R) [4-2H2] 2-Amino-3-Butenoic Acid (Vinylglycine) and (R) [4-2H2, 5-2H3] Methionine
- 1 April 1989
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 19 (7-8) , 1137-1145
- https://doi.org/10.1080/00397918908054516
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.Keywords
This publication has 9 references indexed in Scilit:
- 3-Halovinylglycines. Efficient irreversible inhibitors of Escherichia coli alanine racemaseJournal of the American Chemical Society, 1987
- Synthesis of labeled (.+-.)-2-amino-3-butenoic acidsThe Journal of Organic Chemistry, 1986
- Biosynthesis of 1-aminocyclopropanecarboxylic acid: steric course of the reaction at the α-positionJournal of the Chemical Society, Chemical Communications, 1986
- The free radical chemistry of carboxylic esters of 2-selenopyridine--oxide: a convenient synthesis of (L)-vinylglycineTetrahedron, 1985
- Racemization of Amino AcidsPublished by Springer Nature ,1985
- A novel and efficient synthesis of L-vinylglycineTetrahedron Letters, 1984
- Stereochemical analysis of .gamma.-replacement and .gamma.-elimination processes catalyzed by a pyridoxal phosphate dependent enzymeJournal of the American Chemical Society, 1981
- L-VinylglycineThe Journal of Organic Chemistry, 1980
- Derivate von L‐Methionin‐sulfoxyd und ihre Verwendung für PeptidsynthesenHelvetica Chimica Acta, 1961