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Current Radiopharmaceuticals

Editor-in-Chief

ISSN (Print): 1874-4710
ISSN (Online): 1874-4729

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

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

Volume 1, Issue 2, 2008

Page: [122 - 124] Pages: 3

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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