A simple convenient synthesis of l‐[4‐13C]glutamine |
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| Authors: | Kokoro Nagasawa Atsushi Kishida Masahiro Kajiwara Tomoyuki Kanamatsu Kazuhiko Takatori |
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| Institution: | 1. Department of Synthetic Organic Chemistry, Meiji Pharmaceutical University, Kiyose‐shi, Tokyo, Japan;2. Department of Environmental Engineering for Symbiosis, Faculty of Engineering, Soka University, Hachioji, Tokyo, Japan |
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| Abstract: | l ‐4‐13C]Glutamine was synthesized from sodium 2‐13C]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)2‐13C]acetate prepared from d ‐serine and sodium 2‐13C]acetate, respectively, gave (4S)‐4‐(2‐ethoxycarbonyl2‐13C]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‐4‐13C]glutamine (Cbz = benzyloxycarbonyl). Finally, removal of the Cbz group gave l ‐4‐13C]glutamine. l ‐4‐13C]Glutamine can be prepared in fewer steps and higher yield by this method compared with previously reported methods. |
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| Keywords: | stable labeled synthesis C‐13 glutamine serine amino acid Wittig reaction |
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