1772-03-8 Usage
Uses
1. Used in Pharmaceutical Quality Control:
D(+)-Galactosamine hydrochloride is used as a secondary standard for ensuring the quality and consistency of pharmaceutical products, providing a reliable and cost-effective alternative to in-house working standards.
2. Used in Anti-inflammatory Applications:
D(+)-Galactosamine hydrochloride is used as an inhibitor for COX-2, preventing COX-2 N-glycosylation and increasing COX-2 protein turnover in a proteasome-dependent manner, which helps in reducing inflammation.
3. Used in Hepatic Failure Research:
D(+)-Galactosamine hydrochloride is used in combination with lipopolysaccharides (LPS) to induce models of acute hepatic failure (LPS/D-GalN-induced liver injury, hepatitis) for therapeutic research. This helps in the development of new drugs to treat liver-related conditions.
4. Used in Liver Injury and Inflammation Research:
D(+)-Galactosamine hydrochloride is used to induce liver injury, inflammatory liver injury, and acute liver failure (ALF) in mice, providing a valuable tool for researchers to study the mechanisms and potential treatments for these conditions.
Biochem/physiol Actions
Galactosamine (D-GalN) is synthesized from galactose and is potential hepatotoxic agent. D-GalN in combination with lipopolysaccharide leads to the development of lethal liver injury and hepatic failure. It sensitizes cells to the toxic effects of the cytokine in particular the tumor necrosis factor(TNF).
Synthesis
A preparation process of D-galactosamine hydrochloride, adding 500ml absolute ethanol into a 1000ml three-necked flask with a reflux condenser, a stirrer and a thermometer, stirring at room temperature and adding 100g of dimethyl dodecyl respectively Tetradecylamine and 500g of solid-supported silica were heated to 110°C within 30 minutes, kept in reflux for 5 hours and then lowered to 29°C, filtered and dried to obtain 589g of organic amine solid-supported catalyst. In a 1000ml three-necked flask with a stirrer and a thermometer, 190g of 5-methyltryptamine hydrochloride and 600ml of dimethylamide were respectively added, 59g of organic amine solid-supported catalyst and 150g of chloropropene were added, and the reaction was carried out for eight hours at room temperature. Liquid filtration, the obtained filtrate was evaporated to dryness and dissolved in 1150ml of isopropanol, and 89ml of 36wt% hydrochloric acid was added to hydrochloride to obtain 130.32g of white crystals of 2-amino-2-deoxy-D-galactose hydrochloride with a yield of 42.05%.
Purification Methods
Dissolve the hydrochloride in a small volume of H2O. Then add three volumes of EtOH, followed by acetone until faintly turbid and keep overnight in a refrigerator. [Roseman & Ludoweig J Am Chem Soc 76 301 1954, Beilstein 4 IV 2024.]
Check Digit Verification of cas no
The CAS Registry Mumber 1772-03-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,7,7 and 2 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1772-03:
(6*1)+(5*7)+(4*7)+(3*2)+(2*0)+(1*3)=78
78 % 10 = 8
So 1772-03-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H13NO5.ClH/c7-3-5(10)4(9)2(1-8)12-6(3)11;/h2-6,8-11H,1,7H2;1H/t2-,3-,4+,5-,6+;/m1./s1
1772-03-8Relevant articles and documents
Synthesis of N-protected galactosamine building blocks from D-tagatose via the heyns rearrangement
Wrodnigg, Tanja M.,Lundt, Inge,Stuetz, Arnold E.
, p. 33 - 41 (2007/10/03)
N-Acetyl-D-galactosamine (11), a very important naturally occurring building block of oligosaccharides, is easily accessible via the Heyns rearrangement of D-tagatose (3) with benzylamine. The short and efficient synthesis of various differently N-protected D-galactosamine derivatives is reported. Copyright Taylor & Francis Group, LLC.
Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals
-
, (2008/06/13)
O-acetylated glycals react with ceric ammonium nitrate in the presence of sodium azide to provide, in good yield, O-acetylated 2-azido-2-deoxy glycosyl nitrates. These nitrates can be used to prepare 2-amino-2-deoxy sugars, such as D-galactosamine and lactosamine. The O-acetylated 2-azido-2-deoxy glycosyl nitrates can alternately be converted to O-acetylated 2-azido-2-deoxy glycosyl halides which are useful in the preparation of O-acetylated 2-azido-2-deoxy glycosides, which in turn can be reduced to 2-amino-2-deoxy glycosides. Of particular interest are the syntheses of 2-amino-2-deoxy glycosides which correspond to the terminal units of the antigenic determinant for the human A blood group. Attachment of these glycosides to a solid support provides immunoabsorbents which efficiently and preferentially absorb anti-A antibodies from blood plasma.
