ChEBI: 5-methyltryptophan is a tryptophan derivative that is tryptophan substituted by a methyl group at position 5 of the indole ring. It is a non-proteinogenic alpha-amino acid and a tryptophan derivative.
5-Methyl-DL-tryptophan inhibits the synthesis of anthranilate compounds th at are the first steps in the biosynthesis of tryptophan in Neurospora crassa. 5-Methyl-DL-tryptophan is a corepressor of the E. coli trp repressor.', '5-Methyl-DL-tryptophan may be used to select genetic mutants of PS strain of Methanococcus voltae (archaebacteria). 5-Methyl-tryptophan is a repressor trp operon expression. 5-Methyl-tryptophan is a substrate for tryptophanase. 5-Methyl-tryptophan inhibits the induction of anthranilate synthase activity by elicitors in oats.
Crystallise dl-5-methyltryptophan from aqueous EtOH after dissolving it in aqueous NaOH, precipitating with AcOH, filtering the solid off and drying for 24hours at 50o. [Jackman & Archer J Am Chem Soc 68 2105 1946, Beilstein 22 IV 6815.] The picrate crystallises from MeOH with m 202o(dec). The N-phenylcarbamoyl derivative crystallises from aqueous MeOH with m 202o. [Gordon & Jackson J Biol Chem 110 151, 154 1935.]
