25020-15-9

Basic information

• Product Name: 1-(N-tryptophan)-1-deoxyfructose
• Synonyms: 1-(N-tryptophan)-1-deoxyfructose;Fructose-tryptophan (Mixture of diastereoMers);(S)-1-[[1-Carboxy-2-(1H-indol-3-yl)ethyl]aMino]-1-deoxy-D-fructose;D-Fructose-tryptophan;Fructose-L-tryptophan;N-(1-Deoxy-D-fructos-1-yl)-L-tryptophan
• CAS NO: 25020-15-9
• Molecular Formula: C₁₇H₂₂N₂O₇
• Molecular Weight: 365.35784
• Product Categories: Amino Acids & Derivatives;Apoptosis;Carbohydrates & Derivatives;Amino Acids & Derivatives, Apoptosis, Carbohydrates & Derivatives
• Mol File: 25020-15-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: >125°C (dec.)
• Boiling Point: 786°Cat760mmHg
• Flash Point: 429.2°C
• Appearance: /
• Density: 1.511g/cm³
• Vapor Pressure: 5.02E-26mmHg at 25°C
• Refractive Index: 1.68
• Storage Temp.: -20?C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 2.10±0.10(Predicted)
• CAS DataBase Reference: 1-(N-tryptophan)-1-deoxyfructose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(N-tryptophan)-1-deoxyfructose(25020-15-9)
• EPA Substance Registry System: 1-(N-tryptophan)-1-deoxyfructose(25020-15-9)

Safety Data

• Hazardous Substances Data: 25020-15-9(Hazardous Substances Data)

Usage

Description

1-(N-tryptophan)-1-deoxyfructose, also known as an Amadori compound, is a yellow solid with unique chemical properties. It has the potential to alter cellular adhesion, inhibit cancer metastasis, and induce apoptosis, making it a promising candidate for various applications in the pharmaceutical and medical industries.

Uses

Used in Pharmaceutical Industry:
1-(N-tryptophan)-1-deoxyfructose is used as a pharmaceutical agent for its ability to alter cellular adhesion, which can help in inhibiting cancer metastasis and inducing apoptosis. This makes it a potential candidate for the development of new drugs targeting various types of cancer.
Used in Medical Research:
In the field of medical research, 1-(N-tryptophan)-1-deoxyfructose can be utilized as a research tool to study the mechanisms behind cellular adhesion, cancer metastasis, and apoptosis. 1-(N-tryptophan)-1-deoxyfructose can provide valuable insights into the development of novel therapeutic strategies for cancer treatment.
Used in Drug Delivery Systems:
Similar to gallotannin, 1-(N-tryptophan)-1-deoxyfructose can also be incorporated into drug delivery systems to enhance its bioavailability and therapeutic outcomes. By employing various organic and metallic nanoparticles as carriers, the compound can be effectively delivered to target cancer cells, improving its overall efficacy in cancer treatment.

InChI:InChI=1/C17H22N2O7/c20-8-14(22)16(24)15(23)13(21)7-19-12(17(25)26)5-9-6-18-11-4-2-1-3-10(9)11/h1-4,6,12,14-16,18-20,22-24H,5,7-8H2,(H,25,26)/t12-,14+,15+,16+/m0/s1

Upstream product

• 50-99-7 D-glucose 
• 73-22-3 L-Tryptophan 

Downstream Products

• 3458-28-4 D-Mannose 
• 50-99-7 D-glucose 
• 73-22-3 L-Tryptophan 

Relevant articles and documents

The role of methylglyoxal in the non-enzymatic conversion of tryptophan, its methyl ester and tryptamine to 1-acetyl-β-carbolines

Non-enzymatic modification of l-tryptophan (1) and its metabolites and derivatives with aldehydes, via the Pictet-Spengler reaction, affords β-carbolines. Here we demonstrate that methylglyoxal (2) generates 1-acetyl-β-carbolines from tryptophan (1), from its methyl ester (6) and from tryptamine (4); however, 2 did not generate 1-(1-hydroxyethyl)-β-carboline derivates. HPLC analysis of model reaction systems showed formation of 1-acetyl-β-carboline (3) and 1-acetyl-β-carboline-3-carboxylic acid (5) during incubation of 1 and 2, at pH 5.7 and 7.4, at 100 °C, and only 5 at 37 °C, at the same pH values, with limited access of oxygen. Aerobic conditions caused higher formation of 3 at 37 °C at both pH values, while, at higher temperature, the same effect was only observed at pH 5.7. Lack of oxygen did not much influence the formation of 3 or 5 at both pH and temperature values, in comparison with the formation at limited access of oxygen. Incubation of 2 and 6 generated methyl-1-acetyl-β-carboline-3-carboxylate (7) together with 3 and 5 as a result of hydrolysis of 6 into 1 and, partially, 7 into 5, while in incubation mixtures of 2 and 4 only unstable 1-acetyl-3,4-dihydro-β-carboline (8) was observed. Incubation of 1 with d-glucose as well as incubation of tryptophan with Amadori product 18 under similar conditions did not generate carbolines 3 or 5. For the first time, we were able to demonstrate the presence of 1-acetyl-β-carboline-3-carboxylic acid (5) in some commercially available ketchups and in previously heated tomato concentrate.

Formation of tetrahydro-β-carbolines and β-carbolines during the reaction of L-tryptophan with D-glucose

The reaction of L-tryptophan (Trp) with D-glucose under conditions that can occur during food processing and preparation was studied by high- performance liquid chromatography with diode array detection (HPLC/DAD). Besides the well-established glucose-tryptophan Amadori product (AP), (1R,3S)-1-(D-gluco-1,2,3,4,5-pentahydroxypentyl)-1,2,3,4-tetrahydro-β- carboline-3-carboxylic acid (PHP-THβC) was identified as an important product of this reaction. For preparation, PHPTHβC was obtained in high yields when Trp and D-glucose were reacted under strongly acidic conditions after heating in methanol. At elevated reaction temperatures (150 °C) 1- acetyl-β-carboline (acetyl-βC), was detected in significant concentrations. The mixtures were heated under variations of reaction time and temperature, and AP, PHP-THβC, and acetyl-βC were quantified. In the presence of air oxygen or mild, food relevant oxidants, such as L-dehydroascorbic acid, PHP- THβC was readily oxidized to a product that was identified as the previously unknown 1-(D-gluco-1,2,3,4,5-pentahydroxypentyl)-β-carboline (PHP-βC). Formation of PHP-THβC and PHP-βC in foodstuffs would deserve particular interest because multiple physiological activity of THβC and βC derivatives has been shown previously.