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Synthesis of L-glutamine-S-14C, L-glutamic acid-5-14C, and L-ornithine-5-14C

✍ Scribed by Miloš Havránek; Hana Kopecká-Schadtová; Karel Vereš

Publisher
John Wiley and Sons
Year
1970
Tongue
French
Weight
535 KB
Volume
6
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

On alkylation of K^14^CN with the methyl ester of L‐α‐benzyl‐oxycarbonylamino‐γ‐bromobutyric acid, the methyl ester of L‐α‐benzyloxycarbonylamino‐γ‐cyano‐^14^C‐butyric acid (II) was obtained The latter was submitted to mild alkaline hydrolysis to yield the free nitrilo acid III which on treatment with hydrogen bromide solution in acetic acid gave L‐glutamine‐5‐^14^C in one reaction step. L‐Ornithine‐5‐^14^C was prepared by catalytic hydrogenation of the nitrilo ester II, and L‐glutamic‐5‐^14^C acid was obtained on acid hydrolysis of the same compound (II). The activated ester (2, 4, 5‐trichlorophenyl ester) of acid III may serve as a suitable intermediate for the preparation of glutamine or ornithine peptides. All prepared substances were optically active L‐forms.

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