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Synthesis of deuterium enriched L‐glutamine and 4‐aminobutanamide from pyridazinones
Author(s) -
Stogniew Martin,
Geelhaar Linda A.,
Callery Patrick S.
Publication year - 1981
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580180615
Subject(s) - chemistry , raney nickel , decarboxylation , deuterium , glutamine , stereospecificity , yield (engineering) , hydrogen , ammonia , stereochemistry , medicinal chemistry , amino acid , organic chemistry , catalysis , biochemistry , physics , materials science , quantum mechanics , metallurgy
A convenient method is presented for the preparation of the amino acid glutamine and its decarboxylation product 4‐amino‐ butanamide (GABAMIDE) enriched with deuterium. In a single step, 6‐carboxy‐3(2H)‐pyridazinone was reduced with deuterium gas to give racemic glutamine‐2,3,4‐ 2 H 3 . L‐Glutamine‐2,3,4‐ 2 H 3 was prepared by the stereospecific deacetylation of N 2 ‐acetylglutamine‐2,3,4‐ 2 H 3 with acylase I. 4‐Aminobutanamide‐2,3,4‐ 2 H 3 was synthesized from 3(2H)‐pyridazinone in two steps. Reduction of 3(2H)‐pyridazinone with deuterium gas gave the intermediate, 1,4,5,6‐tetrahydro‐3(2H)‐pyridazinone‐4,5,6‐ 2 H 3 , which was further reduced with Raney nickel and hydrogen to yield 4‐aminobutanamide‐2,3,4‐ 2 H 3 .