title: A simple convenient synthesis of L-[4-13C]glutamine.
abstract: 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.
authors.affiliation: Department of Synthetic Organic Chemistry, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose-shi, Tokyo, 204-8588, Japan.
authors.forename: Kokoro
authors.initials: K
authors.lastname: Nagasawa
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kishida
authors.forename: Masahiro
authors.initials: M
authors.lastname: Kajiwara
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Kanamatsu
authors.forename: Kazuhiko
authors.initials: K
authors.lastname: Takatori
mesh_terms: D002247:Carbon Isotopes / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D005973:Glutamine / Q000138:chemical synthesis*
chemical_list: D002247:Carbon Isotopes; D005973:Glutamine
keywords: C-13; Wittig reaction; amino acid; glutamine; serine; stable labeled synthesis