D-Fructose, 1-((1-carboxy-2-(1H-indol-3-yl)ethyl)amino)-1-deoxy-, (S)-

Base Information

• Chemical Name: D-Fructose, 1-((1-carboxy-2-(1H-indol-3-yl)ethyl)amino)-1-deoxy-, (S)-
• CAS No.: 25020-15-9
• Molecular Formula: C17H22 N2 O7
• Molecular Weight: 366.371
• DSSTox Substance ID: DTXSID501280884
• Mol file: 25020-15-9.mol

Synonyms:1-(N-L-tryptophan)-1-deoxy-D-glucose;1-(N-tryptophan)-1-deoxyfructose;N-(1-deoxy-D-fructos-1-yl)-L-tryptophan;Trp-Fru

Chemical Property of D-Fructose, 1-((1-carboxy-2-(1H-indol-3-yl)ethyl)amino)-1-deoxy-, (S)-

Chemical Property:

• Vapor Pressure: 5.02E-26mmHg at 25°C
• Melting Point: >125°C (dec.)
• Boiling Point: 786°Cat760mmHg
• PKA: 2.10±0.10(Predicted)
• Flash Point: 429.2°C
• PSA: 163.11000
• Density: 1.511g/cm³
• LogP: -1.21180
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -3.6
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 366.14270105
• Heavy Atom Count: 26
• Complexity: 490

Purity/Quality:

98%Min ^*data from raw suppliers

Fructose-tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CC(C(=O)O)NCC(=O)C(C(C(CO)O)O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CN2)C[C@@H](C(=O)O)NCC(=O)[C@H]([C@@H]([C@@H](CO)O)O)O
• Uses: An Amadori compound having the potential to alter cellular adhesion, inhibit cancer metastasis and induce apoptosis.

Technology Process of D-Fructose, 1-((1-carboxy-2-(1H-indol-3-yl)ethyl)amino)-1-deoxy-, (S)-

There total 2 articles about D-Fructose, 1-((1-carboxy-2-(1H-indol-3-yl)ethyl)amino)-1-deoxy-, (S)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 29.0%

D-glucose (50-99-7) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → N-(1-deoxy-D-fructos-1-yl)-L-tryptophan dihydrate (25020-15-9)

Guidance literature:

D-glucose; L-Tryptophan; With potassium hydroxide; In methanol; at 70 ℃; for 2h;

With acetic acid; In methanol; at 70 ℃; for 0.5h; Further stages.;

DOI:10.1016/j.bmc.2008.04.002

Reference yield:

D-glucose (50-99-7) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → N-(1-deoxy-D-fructos-1-yl)-L-tryptophan dihydrate (25020-15-9) + 1-acetyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid + cis-(1R,3S)-1-(1,2,3,4,5-pentahydroxypentyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (252340-31-1)

Guidance literature:

With phosphate buffer; pH=5; Further Variations:; Temperatures; Product distribution; Heating;

DOI:10.1021/jf991237l

Reference yield:

N-(1-deoxy-D-fructos-1-yl)-L-tryptophan dihydrate (25020-15-9) → D-Mannose (3458-28-4) + D-glucose (50-99-7) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7)

Guidance literature:

In phosphate buffer; at 37 ℃; Kinetics;

DOI:10.1016/j.bmc.2008.04.002

upstream raw materials:

D-glucose

L-Tryptophan

Downstream raw materials:

D-Mannose

D-glucose

L-Tryptophan

Refernces

• 1、 Adrover, Miquel,Vilanova, Bartolome,Frau, Juan,Munoz, Francisco,Donoso, Josefa. "The pyridoxamine action on Amadori compounds: A reexamination of its scavenging capacity and chelating effect". . p. 5557 - 5569. Retrieved 2008/12/20.
• 2、 Roeper, Harald,Roeper, Siyka,Heyns, Kurt,Meyer, Bernd. "N.M.R. SPECTROSCOPY OF N-(1-DEOXY-D-FRUCTOS-1-YL)-L-AMINO ACIDS ("FRUCTOSE-AMINO ACIDS")". . p. 183 - 196. Retrieved 2007/10/02.