99295-79-1

Basic information

• Product Name: 5-Methyl-D-tryptophan
• Synonyms: (R)-2-amino-3-(5-methyl-1H-indol-3-yl)propanoic acid;REF DUPL: 5-Methyl-D-tryptophan;D-5-Methyltryptophan;D-Tryptophan, 5-methyl-;5-Methyl-D-tryptophan;H-D-Trp(5-Me)-OH
• CAS NO: 99295-79-1
• Molecular Formula: C₁₂H₁₄N₂O₂
• Molecular Weight: 218.25176
• Mol File: 99295-79-1.mol

Chemical Properties

• Boiling Point: 455.1 °C at 760 mmHg
• Flash Point: 229.1 °C
• Appearance: /
• Density: 1.313
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 5-Methyl-D-tryptophan(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methyl-D-tryptophan(99295-79-1)
• EPA Substance Registry System: 5-Methyl-D-tryptophan(99295-79-1)

Safety Data

• Hazardous Substances Data: 99295-79-1(Hazardous Substances Data)

Usage

Uses

Used in Cancer Therapy:
5-Methyl-D-tryptophan is utilized as an inhibitor of the enzyme indoleamine 2,3-dioxygenase (IDO), which plays a role in immune evasion by tumor cells. By inhibiting IDO activity, this modified tryptophan may contribute to the development of cancer therapeutics, potentially enhancing the body's immune response against cancer cells.
Used in Biological Research:
5-Methyl-D-tryptophan serves as a valuable tool in the study of protein and enzyme structure and function within biological systems. Its unique interactions with biological molecules can provide insights into the mechanisms of various biological processes and aid in the development of new therapeutic strategies.

Upstream product

• 951-55-3 5-methyl-DL-tryptophan 
• 5211-23-4 N-carbobenzyloxy-L-proline methyl ester 
• 93271-97-7 1-benzyl 2-methyl (2S)-5-hydroxypyrrolidine-1,2-dicarboxylate 
• 93272-07-2 5-methyl-N_b-methoxycarbonyl-L-tryptophan methyl ester 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 74761-41-4 (S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 147-85-3 L-proline 
• 93299-30-0 N-methoxycarbonyl-L-glutamine methyl ester 
• 93271-96-6 (2S,5RS)-1,2-dimethyl-5-hydroxypyrrolidine-1,2-dicarboxylate 
• 93271-98-8 N-methoxycarbonyl-4-cyano-L-2-aminobutyric acid methyl ester 
• 93272-12-9 5-methyl-N_b-benzyloxycarbonyl-L-tryptophan methyl ester 
• 83541-81-5 (S)-dimethyl pyrrolidine-1,2-dicarboxylate 
• 93299-41-3 5-methyl-L-tryptophan methyl ester 
• 93272-14-1 5-methyl-N_b-benzyloxycarbonyl-L-tryptophan 

Relevant articles and documents

Chiral ligand-exchange resolution of underivatized amino acids on a dynamically modified stationary phase for RP-HPTLC

The synthesis of Spi(τ-dec), derived from the selective alkylation of L-spinacine (4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid) at the τ-nitrogen of its heteroaromatic ring, with a linear hydrocarbon chain of 10 carbon atoms, is described here for the first time. Spi(τ-dec) was successfully employed in the past to prepare home-made chiral columns for chiral ligand-exchange high-performance liquid chromatography. In the present article a new method is described, using Spi(τ-dec) as a chiral selector in high-performance thin-layer chromatography (HPTLC): commercial hydrophobic plates were first coated with Spi(τ-dec) and then treated with copper sulfate. The performance of this new chiral stationary phase was tested against racemic mixtures of aromatic amino acids, after appropriate optimization of both the conditions of preparation of the plates and the mobile phase composition. The enantioselectivity values obtained for the studied compounds were higher than those reported in the literature for similar systems. The method employed here for the preparation of chiral HPTLC plates proved practical, efficient, and inexpensive. Chirality 26:313-318, 2014. 2014 Wiley Periodicals, Inc.

COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.

Substituent Effects on the Spectral, Acid-Base, and Redox Properties of Indolyl Radicals: A Pulse Radiolysis Study

Spectral and acid-base properties and reduction potentials of various substituted indolyl radicals were studied by pulse radiolysis in aqueous solutions at 20 deg C.Except for the 5-methoxyindolyl and 5-carboxyindolyl radicals, the spectra of the substituted indolyl radicals resemble the previously published 320- and 520-nm spectra of the neutral and 330- and 580-nm spectra of the cation indolyl and tryptophan radicals.The substitution of indolyl radical cation by electron-attracting groups (positive ?+) results in a blue shift of the 580-nm band by ca. 30 nm,, whereas the spectra of methylindolyl (?+ = -0.31) are similar to those of unsubstituted indolyl radicals.The 430- and 455-nm bands appearing in the spectra of the 5-carboxyindolyl and 5-methoxyindolyl radical cations, respectively, indicate even stronger interaction of the unpaired electron with the 5-substituent.The radical cations of various indole-3-acetic acids decarboxylate at pH values below their pKa to produce allyl radicals.The 5-bromoindolyl radical undergoes solvolysis to 5-hydroxyindolyl radical in acidic and alkaline media.The dissociation constants and reduction potentials of the substituted indolyl radicals correlate with the Brown substituent constants: pKr = 4.14 - 2.13Σ?+, correlation coefficient 0.987, and E0/0.059 = 22.29 + 3.5Σ?+, correlation coefficient 0.980.The ρ values from these correlations (-2.13 and 3.5) are similar to that of the Hammett correlation of the dissociation constants of the protonated indole nitrogen in various substituted indoles, ρ = -2.49, but smaller than the ρ value of the dependence on the substituent of the reduction potentials of phenoxyl radicals, ρ = 5.4.

Syntheses of Substituted L- and D-Tryptophans

Several 5-substituted nb-methoxycarbonyl-L- and -D-tryptophan derivatives were synthesized from proline by a new route involving electrochemical oxidation, as well as by the known procedures.Removal of the Nb-methoxycarbonyl group was accomplished by treatment with Me3SiI in refluxing chloroform, then alkaline hydrolysis of the methyl esters afforded 5-substituted L- and D-tryptophans with high optical purities.Keywords - L-tryptophan 5-substituted; D-tryptophan 5-substituted; anodic oxidation; N-methoxycarbonyl group deprotection; Fischer indole synthesis; iodotrimethylsilane