A Synthesis of l-Proline from l-Glutamine
- 1 January 1963
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 36 (1) , 25-29
- https://doi.org/10.1246/bcsj.36.25
Abstract
1. Novel syntheses of optically active proline and ornithine from optically active glutamine are described. 2. Carbobenzoxy-l-glutamine esters were dehydrated to γ-cyano-α-l-carbobenzoxyaminobutyric acid esters with p-toluenesulfonyl chloride, phosphorous oxychloride or thionyl chloride. 3. Hydrogenation of γ-cyano-α-l-carbobenzoxyaminobutyric acid esters in aqueous solvent systems were effected by silk-palladium catalyst to yield mainly l-proline. 4. By hydrogenation in the presence of Raney nickel in non-aqueous solvent, l-ornithine was obtained.Keywords
This publication has 11 references indexed in Scilit:
- Studies on the Silk-Rhodium CatalystBulletin of the Chemical Society of Japan, 1962
- Studies on the Silk-platinum Catalyst. II. General PropertiesBulletin of the Chemical Society of Japan, 1961
- Synthesis of β-Cyano-L-alanine and γ-Cyano-α-L-aminobutyric Acid, Dehydration Products of L-Asparagine and L-Glutamine; a New Synthesis of Amino Acid NitrilesThe Journal of Organic Chemistry, 1961
- Studies on the Silk-platinum Catalyst. I. Its Preparation and ActivityBulletin of the Chemical Society of Japan, 1961
- Studies on the Silk-Palladium Catalyst. III. Physicochemical CharacterizationBulletin of the Chemical Society of Japan, 1959
- Amino-acids and peptides. XXV. Dehydration of derivatives of asparagine and glutamine; A new route to α,γ-diaminobutyric acid, ornithine, and arginineCollection of Czechoslovak Chemical Communications, 1959
- Synthesis of Two Protected Hexapeptides Containing the N-Terminal and C-Terminal Sequences of Arginine-Vasopressin1Journal of the American Chemical Society, 1958
- Une nouvelle synthèse de l'oxytocineHelvetica Chimica Acta, 1955
- Imides from Asparagine and Glutamine1Journal of the American Chemical Society, 1954
- The synthesis of glutamine and asparagine peptides and of glutamineArchives of Biochemistry and Biophysics, 1952