SYNTHESIS OF (13)C AND (15)N LABELED (S)-TRYPTOPHAN

Article abstract of DOI:10.1016/0040-4020(82)85150-8

(R,S)-serine-1-(13)C was incubated in a culture of Escherichia coli cells to produce (S)-tryptophan-1-(13)C.Bromoacetyl bromide-2-(13)C was converted to bromoacetanilide and cyclization of the anilide, followed by reduction and dehydrogenation furnished indole-3-(13)C.Indole-(15)N was synthesized by known sequences.These (13)C and (15)N isotomers of indole were converted by commercially available, lyophilized E. coli to furnish (S)-tryptophan-γ-(13)C and (S)-tryptophan-indole-(15)N, respectively.