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

[ Vol. 1 , Issue. 2 ]

Author(s):

Kazuhiko Takatori, Myonghui Lee and Masahiro Kajiwara   Pages 122 - 124 ( 3 )

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

Affiliation:

Department of Medicinal Chemistry, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose-shi, Tokyo 204-8588, Japan.



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