21495-41-0

Basic information

• Product Name: 2-METHYL-DL-TRYPTOPHAN
• Synonyms: H-2-ME-DL-TRP-OH;DL-2-AMINO-3-(2-METHYLINDOLYL)PROPIONIC ACID;2-METHYL-DL-TRYPTOPHAN;DL-2-methylTryptophan
• CAS NO: 21495-41-0
• Molecular Formula: C₁₂H₁₄N₂O₂
• Molecular Weight: 218.25
• Mol File: 21495-41-0.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 2-METHYL-DL-TRYPTOPHAN(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-DL-TRYPTOPHAN(21495-41-0)
• EPA Substance Registry System: 2-METHYL-DL-TRYPTOPHAN(21495-41-0)

Safety Data

• Hazardous Substances Data: 21495-41-0(Hazardous Substances Data)

Usage

General Description

2-Methyl-DL-tryptophan is a chemical compound that is a derivative of the amino acid tryptophan. It is a chiral compound, meaning it has two enantiomers, designated as D and L forms. 2-METHYL-DL-TRYPTOPHAN is commonly used in the synthesis of pharmaceuticals and as a starting material in the production of various drugs. It has also been investigated for its potential use in the treatment of various medical conditions, such as depression and anxiety. Additionally, 2-Methyl-DL-tryptophan has been studied for its role as a precursor in the synthesis of certain natural products, including alkaloids and peptides. Overall, this compound has a range of potential applications in the fields of medicine and organic chemistry.

Upstream product

• 60587-01-1 N-acetyl-2-methyltryptophan 
• 64-17-5 ethanol 
• 95-20-5 2-methyl-1H-indole 
• 37125-92-1 2-methylgramine 
• 94437-90-8 acetylamino-(2-methyl-indol-3-ylmethyl)-malonic acid diethyl ester 
• 56-45-1 L-serin 

Downstream Products

• 140852-06-8 (R)-2-amino-3-(2-methyl-1H-indol-3-yl)propanoic acid 
• 5416-80-8 2-methyl-1H-indole-3-carbaldehyde 
• 179764-62-6 4-acetylquinoline-2-carboxylic acid 
• 392-12-1 Indole-3-pyruvic acid 
• 63-91-2 L-phenylalanine 
• 1138220-65-1 3-(2-methylindolyl)pyruvic acid 
• 73-22-3 L-Tryptophan 
• 56-86-0 L-glutamic acid 

Relevant articles and documents

Gold-Catalyzed Spirocyclization Reactions of N-Propargyl Tryptamines and Tryptophans in Aqueous Media

N-Propargyl tryptamine and tryptophan derivatives that are readily available from both synthetic and biocatalytic approaches undergo gold-catalyzed dearomative cyclizations in aqueous media to the corresponding spirocyclic derivatives. In addition to the efficiency of the method, operating in aqueous media affords a selective entry to C2-unsubstituted spiroindolenines that have long remained unattainable by Au(I) catalysis. Moderate to excellent yields of the desired spirocyclic products bearing various substituents were obtained.

Processing 2-Methyl- l -Tryptophan through Tandem Transamination and Selective Oxygenation Initiates Indole Ring Expansion in the Biosynthesis of Thiostrepton

Thiostrepton (TSR), an archetypal member of the family of ribosomally synthesized and post-translationally modified thiopeptide antibiotics, possesses a biologically important quinaldic acid (QA) moiety within the side-ring system of its characteristic thiopeptide framework. QA is derived from an independent l-Trp residue; however, its associated transformation process remains poorly understood. We here report that during the formation of QA, the key expansion of an indole to a quinoline relies on the activities of the pyridoxal-5′-phosphate-dependent protein TsrA and the flavoprotein TsrE. These proteins act in tandem to process the precursor 2-methyl- l-Trp through reversible transamination and selective oxygenation, thereby initiating a highly reactive rearrangement in which selective C2-N1 bond cleavage via hydrolysis for indole ring-opening is closely coupled with C2′-N1 bond formation via condensation for recyclization and ring expansion in the production of a quinoline ketone intermediate. This indole ring-expansion mechanism is unusual, and represents a new strategy found in nature for l-Trp-based functionalization.

Peptides containing D-2-Alkyl-Tryptophan

Peptides containing in its amino acid chain a D-2-alkylTryptophan residue wherein the alkyl group has between one and three carbon atoms and having pharmacological activity equal to or greater than that of analogous peptides containing natural unsubstituted D-Tryptophan residues in place of the D-2-alkylTryptophan. These peptides are more resistant to oxidative degradation which usually takes place, for example, in the presence of reactive radicals or during high energy sterilization than unsubstituted Tryptophan containing peptides.