(2R,3R,4R,5R)-2-amino-3,4,5,6-tetrahydroxyhexanal

Base Information

• Chemical Name: (2R,3R,4R,5R)-2-amino-3,4,5,6-tetrahydroxyhexanal
• CAS No.: 7535-00-4
• Molecular Formula: C₆H₁₃NO₅
• Molecular Weight: 179.173
• UNII: 4Y6R29688W
• Nikkaji Number: J16.141A
• Wikidata: Q27127187
• Metabolomics Workbench ID: 61058
• Mol file: 7535-00-4.mol

Synonyms:Galactosamine

Chemical Property of (2R,3R,4R,5R)-2-amino-3,4,5,6-tetrahydroxyhexanal

Chemical Property:

• Vapor Pressure: 5.53E-10mmHg at 25°C
• Melting Point: 185 °C
• Boiling Point: 449.9°C at 760 mmHg
• PKA: 11.21±0.45(Predicted)
• Flash Point: 225.9°C
• PSA: 124.01000
• Density: 1.563g/cm³
• LogP: -2.71210
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: -3.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 179.07937252
• Heavy Atom Count: 12
• Complexity: 142

Purity/Quality:

99%, ^*data from raw suppliers

(2R,3R,4R,5R)-2-Amino-3,4,5,6-tetrahydroxyhexanal 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(C(C(C(C=O)N)O)O)O)O
• Isomeric SMILES: C([C@H]([C@@H]([C@@H]([C@H](C=O)N)O)O)O)O
• Description: Galactosamine is a model hepatotoxicant, induces hepatitis characterized by neutrophilic infiltration, and kills the animal by fulminant hepatic failure. Galactosamine, an amino derivative of sugar galactose, has been used as a model hepatotoxicant since the first reports of hepatotoxicity in late 1970s by Keppler and associates. Galactosamine-induced hepatitis has been a model of choice to study various aspects of liver disease, including mechanisms of toxicant-induced apoptosis and necrosis, liver tissue repair, neutrophil infiltration and transmigration, and the role of endotoxin or lipopolysaccharide (LPS) in initiating liver injury. Humans and animals synthesize galactosamine in the body. Galactosamine (a type of hexosamine) is formed when an amino group replaces one of the hydroxy groups of a sixcarbon sugar, or hexose. The human body utilizes uridine diphosphate (UDP)-N-acetyl-D-glucosamine or glucosamine as a precursor to synthesize this compound, and is most often found in the form N-acetyl-D-galactosamine (often referred to as N-acetylgalactosamine). Most importantly, galactosamine is a constituent of hyaluronic acid, a powerful water-binding agent. Many different types of tissues in human body contain hyaluronic acid, which acts as a lubricating agent in the synovial fluid of joints and in connective tissues. Hyaluronic acid also acts as a lubricating agent in the vitreous humor of the eyeball. Hyaluronic acid has considerable medicinal value; it is often used in wound healing, burn dressings, osteoarthritis treatment, cataract or corneal transplantation surgery, and various types of plastic surgeries.

Technology Process of (2R,3R,4R,5R)-2-amino-3,4,5,6-tetrahydroxyhexanal

There total 21 articles about (2R,3R,4R,5R)-2-amino-3,4,5,6-tetrahydroxyhexanal 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:

O-polysaccharide of Escherichia coli O102 → L-Rhamnose (3615-41-6,478518-52-4) + D-glucose (50-99-7) + D-Galactose (59-23-4) + D-galactosamine (1948-54-5,2494-50-0,2636-92-2,3416-24-8,6915-39-5,7535-00-4,14307-02-9,14307-08-5,14307-09-6,14307-12-1,14307-14-3,14635-95-1,26315-48-0,27799-64-0,27799-65-1,69839-78-7,72904-60-0)

Guidance literature:

With water; trifluoroacetic acid; at 120 ℃; for 2h;

DOI:10.1016/j.carres.2012.07.024

Reference yield:

Acinetobacter lwoffii EK30A O-antigen → D-homoserine (6027-21-0,119736-88-8) + 2-amino-2,6-dideoxy-D-galactose (6931-59-5) + D-Galactose (59-23-4) + D-galactosamine (1948-54-5,2494-50-0,2636-92-2,3416-24-8,6915-39-5,7535-00-4,14307-02-9,14307-08-5,14307-09-6,14307-12-1,14307-14-3,14635-95-1,26315-48-0,27799-64-0,27799-65-1,69839-78-7,72904-60-0)

Guidance literature:

With water; trifluoroacetic acid; at 120 ℃; for 3h;

DOI:10.1039/c004090h

Reference yield:

Salmonella enterica subsp. enterica serovar Telaviv (I 28:y:e,n,z15) KOS 106 O-polysaccharide → D-ribose (50-69-1) + D-glucose (50-99-7) + D-Galactose (59-23-4) + D-galactosamine (1948-54-5,2494-50-0,2636-92-2,3416-24-8,6915-39-5,7535-00-4,14307-02-9,14307-08-5,14307-09-6,14307-12-1,14307-14-3,14635-95-1,26315-48-0,27799-64-0,27799-65-1,69839-78-7,72904-60-0) + 3-amino-3,6-dideoxyglucose (15435-23-1,18118-75-7,32817-12-2,527-38-8)

Guidance literature:

With trifluoroacetic acid; at 120 ℃; for 2h;

DOI:10.1134/S000629791107008X

upstream raw materials:

D-tagatose

2-amino-1,6-anhydro-2-deoxy-β-D-galactopyranose

2-acetamido-1,6-anhydro-2-deoxy-β-D-galactopyranose

2-amino-2-deoxy-D-galactononitrile

Downstream raw materials:

2-amino-2-deoxy-D-galacticol

2-(2,4-dinitro-anilino)-2-deoxy-D-galactose

N-acetylgalactosamine

phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thiol-D-galactopyranoside

Refernces

• 1、 Coppa, Giovanni V.,Galeotti, Fabio,Zampini, Lucia,MacCari, Francesca,Galeazzi, Tiziana,Padelia, Lucia,Santoro, Lucia,Gabrielli, Orazio,Volpi, Nicola. "High-throughput determination of urinary hexosamines for diagnosis of mucopolysaccharidoses by capillary electrophoresis and high-performance liquid chromatography". scheme or table. p. 32 - 42. Retrieved 2012/01/13.
• 2、 Arbatsky, Nikolay P.,Kondakova, Anna N.,Shashkov, Alexander S.,Drutskaya, Marina S.,Belousov, Pavel V.,Nedospasov, Sergei A.,Petrova, Mayya A.,Knirel, Yuriy A.. "Structure of the O-antigen of Acinetobacter lwoffii EK30A; Identification of d-homoserine, a novel non-sugar component of bacterial polysaccharides". experimental part. p. 3571 - 3577. Retrieved 2010/08/21.