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A simple convenient synthesis of l ‐[4‐ 13 C]glutamine
Author(s) -
Nagasawa Kokoro,
Kishida Atsushi,
Kajiwara Masahiro,
Kanamatsu Tomoyuki,
Takatori Kazuhiko
Publication year - 2015
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.3265
Subject(s) - chemistry , glutamine , moiety , yield (engineering) , sodium acetate , carboxylate , carbon 13 nmr , sodium , stereochemistry , organic chemistry , medicinal chemistry , amino acid , biochemistry , materials science , metallurgy
l ‐[4‐ 13 C]Glutamine was synthesized from sodium [2‐ 13 C]acetate in 12 steps and 18% overall yield. A Wittig reaction of (R)‐benzyl 4‐formyl‐2,2‐dimethyloxazolidine‐3‐carboxylate and ethyl 2‐(triphenylphosphoranylidene)[2‐ 13 C]acetate prepared from d ‐serine and sodium [2‐ 13 C]acetate, respectively, gave (4S)‐4‐(2‐ethoxycarbonyl[2‐ 13 C]vinyl)‐2,2‐dimethyloxazolidine‐3‐carboxylic acid α , β‐ isopropylidene group, oxidation of the resulting hydroxyl group to a carboxyl group and transamidation of the ester moiety gave l ‐ N ‐Cbz‐[4‐ 13 C]glutamine (Cbz = benzyloxycarbonyl). Finally, removal of the Cbz group gave l ‐[4‐ 13 C]glutamine. l ‐[4‐ 13 C]Glutamine can be prepared in fewer steps and higher yield by this method compared with previously reported methods.