25197-96-0

Usage

Uses

Used in Pharmaceutical Industry:
5-METHOXY-L-TRYPTOPHAN is used as a reagent for the preparation of anti-HIV agent flazine analogues. Its unique chemical structure allows for the development of new drugs that can potentially combat the HIV virus more effectively.
Used in Chemical Synthesis:
5-METHOXY-L-TRYPTOPHAN serves as an important intermediate in the synthesis of various pharmaceutical compounds, including those with potential applications in the treatment of neurological disorders, cancer, and other diseases. Its versatile structure makes it a valuable starting material for the development of novel therapeutic agents.
Used in Research and Development:
As a compound with unique properties, 5-METHOXY-L-TRYPTOPHAN is utilized in research and development for the study of its biological activities and potential applications in medicine. This includes investigations into its interactions with various biological targets, such as receptors, enzymes, and other proteins, as well as its potential use in drug discovery and development.
Used in Drug Delivery Systems:
Similar to gallotannin, 5-METHOXY-L-TRYPTOPHAN could potentially be incorporated into drug delivery systems to improve the bioavailability and therapeutic outcomes of related pharmaceutical compounds. This may involve the development of novel carriers, such as organic or metallic nanoparticles, to enhance the delivery and efficacy of the compound in treating specific diseases.

InChI:InChI=1/C12H14N2O3/c1-17-8-2-3-11-9(5-8)7(6-14-11)4-10(13)12(15)16/h2-3,5-6,10,14H,4,13H2,1H3,(H,15,16)/t10-/m0/s1

Upstream product

• 28052-84-8 5-methoxytryptophan 
• 93272-02-7 5-trifluoroacetoxy-N_b-methoxycarbonyl-D-tryptophan methyl ester 
• 67010-09-7 N^α-acetyl-5-methoxy-L-tryptophan 
• 2311-25-3 N-acetyl-L-proline methyl ester 
• 147-85-3 L-proline 
• 43167-40-4 N^α-acetyl-5-methoxy-D,L-tryptophan 
• 74761-41-4 (S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 68-95-1 (S)-acetylproline 
• 72458-83-4 5-methoxy-N_b-methoxycarbonyl-L-tryptophan methyl ester 
• 93299-30-0 N-methoxycarbonyl-L-glutamine methyl ester 
• 93271-96-6 (2S,5RS)-1,2-dimethyl-5-hydroxypyrrolidine-1,2-dicarboxylate 
• 154005-67-1 (S)-1-Acetyl-5-hydroxy-pyrrolidine-2-carboxylic acid methyl ester 
• 93271-98-8 N-methoxycarbonyl-4-cyano-L-2-aminobutyric acid methyl ester 
• 93272-00-5 5-methoxy-N_b-acetyl-L-tryptophan methyl ester 

Downstream Products

• 460751-69-3 (S)-N-(fluoren-9-ylmethoxycarbonyl)-5-methoxy-tryptophan 
• 67010-09-7 N^α-acetyl-5-methoxy-L-tryptophan 
• 608-07-1 2-(5-methoxyindol-3-yl)ethylamine 

Relevant academic research and scientific papers

The facile synthesis of a series of tryptophan derivatives

This study reports a facile method for the synthesis of a variety of 5- and 6-substituted tryptophan derivatives that are difficult to prepare using alternative enzymatic approaches. Acylation of an activated amino acid, derived from serine in situ, is coupled with an enzymatic resolution step to furnish enantiopure analogues bearing a range of electron withdrawing and releasing substituents. Isolation of a dehydroalanine derivative as a by-product from some reactions provides some insights into the likely mechanism of the reaction.

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