33468-34-7

Basic information

• Product Name: 6-Methyl-L-tryptophan
• Synonyms: 6-Methyl-L-tryptophan;L-Tryptophan, 6-methyl-;(S)-2-Amino-3-(6-methyl-1H-indol-3-yl)propanoic acid
• CAS NO: 33468-34-7
• Molecular Formula: C12H14N2O2
• Molecular Weight: 218.25176
• EINECS: -0
• Mol File: 33468-34-7.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-Methyl-L-tryptophan(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Methyl-L-tryptophan(33468-34-7)
• EPA Substance Registry System: 6-Methyl-L-tryptophan(33468-34-7)

Safety Data

• Hazardous Substances Data: 33468-34-7(Hazardous Substances Data)

Usage

General Description

6-Methyl-L-tryptophan, also known as 6-Me-TRP, is a modified form of the amino acid L-tryptophan. It contains an additional methyl group attached to the sixth carbon atom of the indole ring, which gives it unique chemical and biological properties. 6-Methyl-L-tryptophan has been studied for its potential therapeutic effects, particularly its ability to inhibit the enzyme indoleamine 2,3-dioxygenase (IDO). This inhibition can modulate the immune response, making it a potential candidate for the treatment of various immune-related disorders, including cancer and inflammatory diseases. Studies have also shown that 6-Methyl-L-tryptophan has anti-inflammatory and neuroprotective properties, making it an interesting compound for further research and potential pharmaceutical development.

Upstream product

• 2280-85-5 6-methyl-DL-tryptophan 
• 3420-02-8 6-methylindole 
• 56-45-1 L-serin 
• 851364-80-2 4-[3-(6-methylindolyl)methyl]-4-hydroxy-2-hydroxyimino-glutalic acid ammonium salt 
• 187028-77-9 N^α-acetyl-6-methyl-D,L-tryptophan 

Downstream Products

• 1991-93-1 6-methyl-L-tryptophan 
• 67008-97-3 6-methyl-D-tryptophan 

Relevant articles and documents

Biocatalysts from cyanobacterial hapalindole pathway afford antivirulent isonitriles against MRSA

Abstract: The emergence of resistance to frontline antibiotics has called for novel strategies to combat serious pathogenic infections. Methicillin-resistant Staphylococcus aureus [MRSA] is one such pathogen. As opposed to traditional antibiotics, bacteriostatic anti-virulent agents disarm MRSA, without exerting pressure, that cause resistance. Herein, we employed a thermophilic Thermotoga maritima tryptophan synthase (TmTrpB1) enzyme followed by an isonitrile synthase and Fe(II)-α-ketoglutarate-dependent oxygenase, in sequence as biocatalysts to produce antivirulent indole vinyl isonitriles. We report on conversion of simple derivatives of indoles to their C3-vinyl isonitriles, as the enzymes employed here demonstrated broader substrate tolerance. In toto, eight distinct L-Tryptophan derived α-amino acids (7) were converted to their bioactive vinyl isonitriles (3) by action of an isonitrile synthase (WelI1) and an Fe(II)-α-ketoglutarate-dependent oxygenase (WelI3) yielding structural variants possessing antivirulence against MRSA. These indole vinyl isonitriles at 10 μg/mL are effective as antivirulent compounds against MRSA, as evidenced through analysis of rabbit blood hemolysis assay. Based on a homology modelling exercise, of enzyme-substrate complexes, we deduced potential three dimensional alignments of active sites and glean mechanistic insights into the substrate tolerance of the Fe(II)-α-ketoglutarate-dependent oxygenase. Graphic abstract: [Figure not available: see fulltext.]

Complete Stereoinversion of l -Tryptophan by a Fungal Single-Module Nonribosomal Peptide Synthetase

Single-module nonribosomal peptide synthetases (NRPSs) and NRPS-like enzymes activate and transform carboxylic acids in both primary and secondary metabolism and are of great interest due to their biocatalytic potentials. The single-module NRPS IvoA is essential for fungal pigment biosynthesis. Here, we show that IvoA catalyzes ATP-dependent unidirectional stereoinversion of l-tryptophan to d-tryptophan with complete conversion. While the stereoinversion is catalyzed by the epimerization (E) domain, the terminal condensation (C) domain stereoselectively hydrolyzes d-tryptophanyl-S-phosphopantetheine thioester and thus represents a noncanonical C domain function. Using IvoA, we demonstrate a biocatalytic stereoinversion/deracemization route to access a variety of substituted d-tryptophan analogs in high enantiomeric excess.

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.