Asymmetric Synthesis of L-[3-13C]Tryptophan

Kazuhiko      Takatori; Myonghui      Lee; Masahiro      Kajiwara

doi:10.2174/1874471010801020122

Abstract

Synthesis of L-[3-13C]tryptophan (2) from N,N-dimethyl[13C]formamide (4) and Dellarias oxazinone 1 as a chiral glycine equivalent was achieved. Vilsmeier reaction of indole (5) and N,N-dimethyl[13C]formamide (4) afforded a good yield of indole-3-[13C]carbaldehyde (3), which was converted to the bromide 8. Diastereoselective alkylation of the enolate of 1 with the bromide 8 proceeded with high diastereoselectivity to give 9. Ethanolysis, hydrogenolysis and hydrolysis of 9 gave L-[3-13C]tryptophan (2).

Keywords: L-[3-13C]tryptophan, labeled amino acid, chiral glycine equivalent, oxazinone

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Current Radiopharmaceuticals

Title: Asymmetric Synthesis of L-[3-13C]Tryptophan

Volume: 1 Issue: 2

Author(s): Kazuhiko Takatori, Myonghui Lee and Masahiro Kajiwara

Affiliation:

Keywords: L-[3-13C]tryptophan, labeled amino acid, chiral glycine equivalent, oxazinone

Abstract: Synthesis of L-[3-13C]tryptophan (2) from N,N-dimethyl[13C]formamide (4) and Dellarias oxazinone 1 as a chiral glycine equivalent was achieved. Vilsmeier reaction of indole (5) and N,N-dimethyl[13C]formamide (4) afforded a good yield of indole-3-[13C]carbaldehyde (3), which was converted to the bromide 8. Diastereoselective alkylation of the enolate of 1 with the bromide 8 proceeded with high diastereoselectivity to give 9. Ethanolysis, hydrogenolysis and hydrolysis of 9 gave L-[3-13C]tryptophan (2).

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Takatori Kazuhiko, Lee Myonghui and Kajiwara Masahiro, Asymmetric Synthesis of L-[3-13C]Tryptophan, Current Radiopharmaceuticals 2008; 1 (2) . https://dx.doi.org/10.2174/1874471010801020122