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Usage

Uses

Used in Pharmaceutical and Medicinal Applications:
(2S)-2-(acetyl-nitroso-amino)-3-(1H-indol-3-yl)propanoic acid is used as a pharmaceutical and medicinal compound for its potential biological activities. Its unique chemical structure may contribute to various therapeutic effects, although further research is required to fully understand its properties and applications in this field.
Used in Research and Development:
(2S)-2-(acetyl-nitroso-amino)-3-(1H-indol-3-yl)propanoic acid serves as a subject of research and development in the scientific community. Its presence in food sources and potential biological activities make it an interesting candidate for exploring new applications and understanding its role in health and disease.

InChI:InChI=1/C13H13N3O4/c1-8(17)16(15-20)12(13(18)19)6-9-7-14-11-5-3-2-4-10(9)11/h2-5,7,12,14H,6H2,1H3,(H,18,19)/t12-/m0/s1

Upstream product

• 1218-34-4 N-AcTrp 
• 1218-34-4 N-acetyl-DL-tryptophan 

Downstream Products

• 1218-34-4 N-AcTrp 
• 1218-34-4 N-acetyl-DL-tryptophan 

Relevant academic research and scientific papers

Comparison of HNO reactivity with tryptophan and cysteine in small peptides

Recent discoveries of important pharmacological properties have drawn attention to the reactivity of HNO (azanone, nitroxyl) with biologically relevant substrates. Apart from its role in thiol oxidation, HNO has been reported to have nitrosative properties, for example, with tryptophan resulting in N-nitrosotryptophan formation. We have investigated the reactivity of HNO with tryptophan and small peptides containing either tryptophan or both a tryptophan and a cysteine residue. Our results point to the more reactive nature of cysteine towards HNO compared with tryptophan.

Kinetics and Mechanism of the Nitrosation of N-Acetyltryptophan and of the Denitrosation of N-Acetyl-N1-nitrosotryptophan

Both the formation and the denitrosation of N-acetyl-N1-nitrosotryptophan have been studied kinetically in aqueous solution at 25 deg C at acidities between 1M-HClO4 and pH 4.A value of 850 l mol-1 has been obtained for the equilibrium constant for the formation of N-acetyl-N1-nitrosotryptophan.At acidities (+>) greater than 0.1M the rate constants for both nitrosation and denitrosation increase linearly with the concentration of acid, and the reaction rates are unaffected by the addition of nucleophiles (Br- and SCN-).The results are consistent with a mechanism for nitrosation where the rate-limiting step is the proton transfer from the protonated N-nitroso species to the medium.For denitrosation the corresponding protonation of the nitrosamine is rate-limiting.These conclusions are confirmed by the results obtained when the reactions are carried out in heavy water.However, in the pH range 1-4 the rates of both nitrosation and denitrosation are independent of the acidity of the medium and are again unaffected by the presence of nucleophiles or buffers.It is suggested that in this region nitrosation occurs at C-3.This is followed by deprotonation and an internal NO migration from C to N which is rate-limiting.This mechanism also accounts for earlier results on the denitrosation reaction at even lower acidities (pH 4-7), where acid catalysis and nucleophilic catalysis are found.Results of experiments in heavy water are compatible with this mechanism.