13081-15-7

Basic information

• Product Name: 2-amino-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)propaneperoxoic acid
• CAS NO: 13081-15-7
• Molecular Formula: C₁₁H₁₂N₂O₄
• Molecular Weight: 236.224
• Mol File: 13081-15-7.mol
• Article Data: 4

Chemical Properties

• Density: 1.388g/cm³
• Refractive Index: 1.597
• CAS DataBase Reference: 2-amino-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)propaneperoxoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)propaneperoxoic acid(13081-15-7)
• EPA Substance Registry System: 2-amino-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)propaneperoxoic acid(13081-15-7)

Safety Data

• Hazardous Substances Data: 13081-15-7(Hazardous Substances Data)

Upstream product

• 73-22-3 L-tryptophan 
• 6536-35-2 oxindolyl-L-alanine 
• 91-56-5 indole-2,3-dione 
• 99985-24-7 2-hydroxyimino-3-(2-oxo-indolin-3-yl)-propionic acid 
• 103646-19-1 (2-oxo-indolin-3-ylidene)-pyruvic acid 
• 54-12-6 Trp 
• 73-22-3 L-Tryptophan 
• 32999-55-6 2-Amino-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)-propionic acid 
• 32999-55-6 oxindolylalanine 

Downstream Products

• 76604-82-5 dioxindolyl-L-alanine 
• 128303-30-0 dioxindolyl-L-alanine 

Relevant articles and documents

Mass spectrometric analysis of oxidized tryptophan

Oxindolylalanine and oxindolylalanine-containing peptides were prepared by treatment of tryptophan and tryptophan-containing peptides with mixtures of dimethyl sulfoxide and hydrochloric acid in acetic acid (DMSO-HCl-HAc). The reaction between tryptophan and DMSO-HCl-HAc was monitored by fast atom bombardment mass spectrometry (FAB-MS) and the proposed chlorotryptophan intermediate in the reaction was observed. Almost complete conversion of tryptophan to oxindolylalanine was obtained in reaction mixtures containing 3.75 M HCl when the reaction was performed in an open tube. A higher HCl concentration (5.5 M) and a closed reaction tube promoted the formation of by-products, such as dioxindolylalanine and 3-chlorooxindolylalanine. Extensive hydrolysis C-terminal of tryptophan was observed when tryptophan-containing peptides were treated with DMSO-HCl-HAc containing 5.5 M HCl, during which the tryptophan residue was modified to dioxindolylalanine lactone. Hydrolysis was not observed in mixtures containing 3.75 M HCl. The presence of oxindolylalanine in peptides could be demonstrated by characteristic peaks in FAB collision-induced dissociation tandem mass spectra.

Oxidative transformation of tryptophan to 3-(2-aminophenyl)-2-pyrrolidone and kynurenine

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