33468-36-9

Usage

Uses

Used in Nutritional Supplements:
(S)-2-AMINO-3-(7-METHYL-1H-INDOL-3-YL)-PROPIONIC ACID is used as a dietary supplement to ensure adequate intake of this essential amino acid, particularly for individuals who may not consume enough through their regular diet. It helps in the synthesis of proteins and supports overall health.
Used in Pharmaceutical Applications:
In the pharmaceutical industry, (S)-2-AMINO-3-(7-METHYL-1H-INDOL-3-YL)-PROPIONIC ACID is used as an active ingredient in the development of medications targeting various health conditions. Its role in serotonin production makes it a potential candidate for treatments related to mood regulation and sleep disorders.
Used in Food Industry:
(S)-2-AMINO-3-(7-METHYL-1H-INDOL-3-YL)-PROPIONIC ACID is used as a food additive to enhance the nutritional value of certain products, particularly those that may be low in essential amino acids. It contributes to the overall protein content and can be used to improve the taste and texture of food items.
Used in Research and Development:
In the field of scientific research, (S)-2-AMINO-3-(7-METHYL-1H-INDOL-3-YL)-PROPIONIC ACID is used as a key compound in studies related to human biology, protein synthesis, and neurotransmitter function. It aids in understanding the mechanisms of various biological processes and the development of new therapeutic strategies.

InChI:InChI=1/C12H14N2O2/c1-7-3-2-4-9-8(6-14-11(7)9)5-10(13)12(15)16/h2-4,6,10,14H,5,13H2,1H3,(H,15,16)

Upstream product

• 933-67-5 7-methyl-1H-indole 
• 4771-50-0 7-methyl-1H-indole-3-carbaldehyde 

Relevant academic research and scientific papers

Preparation method of non-natural L - tryptophan derivative

The invention discloses a preparation method of a non-natural L - tryptophan derivative, which is sequentially subjected to formylation by adopting a cheap and easily available substituted indole compound as a raw material. Cyclization, ring opening, asym

Synthesis method of 7-methyltryptophan

The invention provides a synthesis method of 7-methyl tryptophan, which comprises the following steps: (1) reacting a compound a with a compound b to obtain a compound 1; (2) reacting the compound 1 with water to obtain a compound 2; (3) reacting the compound 2 with hydrogen to obtain a compound 3; and (4) carrying out hydrolysis reaction on the compound 3 to obtain the 7-methyl tryptophan. The method has the advantages of cheap and accessible raw materials, mild reaction conditions, simple equipment requirements and high safety index, and is suitable for large-scale commercial production. Thetotal yield of the 7-methyl tryptophan prepared by the method is as high as 52.6%, and the purity of the 7-methyl tryptophan is as high as 98%. The invention provides a new choice for the commercialproduction process of the 7-methyl tryptophan medicinal intermediate.

Synthesis of tripeptides containing d-Trp substituted at the indole ring, assessment of opioid receptor binding and in vivo central antinociception

The noncationizable tripeptide Ac-d-Trp-Phe-GlyNH2 was recently proposed as a novel minimal recognition motif for μ-opioid receptor. The introduction of different substituents (methyl, halogens, nitro, etc.) at the indole of d-Trp significantly influenced receptor affinities and resulted in serum stability and in a measurable effect on central antinociception in mice after ip administration.

Dimethylallyltryptophan synthase. An enzyme-catalyzed electrophilic aromatic substitution

Dimethylallyltryptophan (DMAT) synthase catalyzes the alkylation of L-tryptophan at C(4) by dimethylallyl diphosphate (DMAPP) in the first pathway-specific step in the biosynthesis of ergot alkaloids. The mechanism of the reaction was studied with analogs of both substrates. Five 7-substituted derivatives of N-acetyltryptophan (2, Z = OCH3, CH3, F, CF3, and NO2) were synthesized. The L enantiomers of the free amino acids were obtained by selective hydrolysis of the racemate using aminoacylase from Aspergillus. In addition, the E and Z fluoromethyl and difluoromethyl analogs of DMAPP (1, Y = CH3, CH2F, CHF2) were prepared. Rates of the enzyme-catalyzed reactions were measured for the dimethylallyl derivatives with L-tryptophan and for the L-tryptophan derivatives with DMAPP. In addition, the relative reactivities of the methanesulfonate derivatives of the DMAPP analogs were determined for solvolysis in aqueous acetone. A Hammett plot for the tryptophan analogs gave a good linear correlation with p = -2.0. In addition, a Hammett plot of the logarithms of the relative rates of solvolysis and enzyme-catalyzed alkylation gave a positive linear correlation. These results indicate that the prenyl-transfer reaction catalyzed by DMAT synthase is an electrophilic aromatic substitution and is mechanistically similar to the electrophilic alkylation catalyzed by farnesyl diphosphate synthase.