Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
A Synthesis of L-Proline from L-Glutamine
Tamio Itoh
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1963 Volume 36 Issue 1 Pages 25-29

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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.

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