Galactosamine

Galactosamine^[1]
Names
	IUPAC name 2-Amino-2-deoxy-D-galactose
	Other names α-D-galactosamine
Identifiers
CAS Number	7535-00-4 ;
3D model (JSmol)	Interactive image ;
ChEBI	CHEBI:60312 ;
ChEMBL	ChEMBL207280 ;
ChemSpider	22576 ;
PubChem CID	24154 ;
UNII	4Y6R29688W ;
	InChI InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4+,5-,6?/m1/s1 Key: MSWZFWKMSRAUBD-GASJEMHNSA-N ; InChI=1/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4+,5-,6?/m1/s1 Key: MSWZFWKMSRAUBD-GASJEMHNBA;
	SMILES O[C@H]1[C@@H](O)[C@H](OC(O)[C@@H]1N)CO;
Properties
Chemical formula	C6H13NO5
Molar mass	179.172 g·mol−1
Melting point	180 °C (356 °F; 453 K) (HCl salt)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Last updated January 20, 2025

Galactosamine is a hexosamine derived from galactose with the molecular formula C₆H₁₃NO₅. This amino sugar is a constituent of some glycoprotein hormones such as follicle-stimulating hormone (FSH) and luteinizing hormone (LH).

Hepatotoxicity

Galactosamine is used to induce hepatitis in rodent liver for research purposes. The result of using galactosamine to induce hepatitis is a disease model in which there is necrosis and inflammation of the liver. This type of tissue damage triggered by galactosamine resembles drug-induced liver disease in humans.^[3]

Mechanism of hepatotoxicity

The proposed mechanism behind galactosamine-induced hepatitis is depletion of the energy source of hepatocytes. In the Leloir pathway galactosamine is metabolized into galactosamine-1-phosphate (by galactokinase) and UDP-galactosamine (by UDP-galactose uridyltransferase). It is hypothesized that this leads to UDP-galactosamine accumulation within cells, and uridine triphosphate (UTP), UDP, and uridine monophosphate (UMP) decrease.^[2] The depletion of high-energy molecules such as UTP leads to a disruption in hepatocyte metabolism. Additionally, other derivatives of uridine such as UDP-glucose are depleted and this interferes with glycogen synthesis in the cell.

Another recent hypothesis states that overexpression of pro-inflammatory cytokines (such as tumor necrosis factor (TNFα) and NFκB-dependent inducible nitric oxide synthase (iNOS) over expression play a role in galactosamine-induced damage to liver cells.^[3]

Related Research Articles

Alcoholic liver disease (ALD), also called alcohol-related liver disease (ARLD), is a term that encompasses the liver manifestations of alcohol overconsumption, including fatty liver, alcoholic hepatitis, and chronic hepatitis with liver fibrosis or cirrhosis.

Hepatotoxicity implies chemical-driven liver damage. Drug-induced liver injury (DILI) is a cause of acute and chronic liver disease caused specifically by medications and the most common reason for a drug to be withdrawn from the market after approval.

<span class="mw-page-title-main">Uridine triphosphate</span> Chemical compound

Uridine-5′-triphosphate (UTP) is a pyrimidine nucleoside triphosphate, consisting of the organic base uracil linked to the 1′ carbon of the ribose sugar, and esterified with tri-phosphoric acid at the 5′ position. Its main role is as substrate for the synthesis of RNA during transcription. UTP is the precursor for the production of CTP via CTP synthetase. UTP can be biosynthesized from UDP by Nucleoside Diphosphate Kinase after using the phosphate group from ATP. UDP + ATP ⇌ UTP + ADP; both UTP and ATP are energetically equal.

<span class="mw-page-title-main">NAPQI</span> Toxic byproduct of acetaminophen

NAPQI, also known as NAPBQI or N-acetyl-p-benzoquinone imine, is a toxic byproduct produced during the xenobiotic metabolism of the analgesic paracetamol (acetaminophen). It is normally produced only in small amounts, and then almost immediately detoxified in the liver.

UTP—glucose-1-phosphate uridylyltransferase also known as glucose-1-phosphate uridylyltransferase is an enzyme involved in carbohydrate metabolism. It synthesizes UDP-glucose from glucose-1-phosphate and UTP; i.e.,

<span class="mw-page-title-main">Tunicamycin</span> Chemical compound

Tunicamycin is a mixture of homologous nucleoside antibiotics that inhibits the UDP-HexNAc: polyprenol-P HexNAc-1-P family of enzymes. In eukaryotes, this includes the enzyme GlcNAc phosphotransferase (GPT), which catalyzes the transfer of N-acetylglucosamine-1-phosphate from UDP-N-acetylglucosamine to dolichol phosphate in the first step of glycoprotein synthesis. Tunicamycin blocks N-linked glycosylation (N-glycans) and treatment of cultured human cells with tunicamycin causes cell cycle arrest in G1 phase. It is used as an experimental tool in biology, e.g. to induce unfolded protein response. Tunicamycin is produced by several bacteria, including Streptomyces clavuligerus and Streptomyces lysosuperificus.

In enzymology, an UDP-glucosamine 4-epimerase is an enzyme that catalyzes the chemical reaction

In enzymology, an UDP-N-acetylglucosamine 2-epimerase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">UDP-N-acetylglucosamine 4-epimerase</span> Class of enzymes

In enzymology, an UDP-N-acetylglucosamine 4-epimerase is an enzyme that catalyzes the chemical reaction

In enzymology, a dolichyl-phosphate alpha-N-acetylglucosaminyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a glycoprotein-N-acetylgalactosamine 3-beta-galactosyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a N-acetyllactosaminide 3-alpha-galactosyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a protein N-acetylglucosaminyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, an UDP-galactose—UDP-N-acetylglucosamine galactose phosphotransferase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">UDP-N-acetylglucosamine diphosphorylase</span> Class of enzymes

In enzymology, an UDP-N-acetylglucosamine diphosphorylase is an enzyme that catalyzes the chemical reaction

In enzymology, a glycoprotein-fucosylgalactoside alpha-N-acetylgalactosaminyltransferase is an enzyme that catalyzes the chemical reaction

(N-acetylneuraminyl)-galactosylglucosylceramide N-acetylgalactosaminyltransferase is an enzyme with systematic name UDP-N-acetyl-D-galactosamine:1-O-(O- - -O-beta-D-galactopyranosyl- -beta-D-glucopyranosyl)-ceramide 4-beta-N-acetyl-D-galactosaminyltransferase. This enzyme catalyses the following chemical reaction:

Beta-1,3-galactosyl-O-glycosyl-glycoprotein beta-1,6-N-acetylglucosaminyltransferase is an enzyme with systematic name UDP-N-acetyl-D-glucosamine:O-glycosyl-glycoprotein 6-beta-N-acetyl-D-glucosaminyltransferase. This enzyme catalyses the following chemical reaction

Acetylgalactosaminyl-O-glycosyl-glycoprotein beta-1,6-N-acetylglucosaminyltransferase (EC 2.4.1.148 with systematic name UDP-N-acetyl-D-glucosamine:N-acetyl-beta-D-glucosaminyl- -N-acetyl-D-galactosaminyl-R 6-beta-N-acetyl-D-glucosaminyltransferase. This enzyme catalyses the following chemical reaction

Uridine diphosphate N-acetylgalactosamine or UDP-GalNAc is a nucleotide sugar composed of uridine diphosphate (UDP) and N-acetyl galactosamine (GalNAc). It is used by glycosyltransferases to transfer N-acetylgalactosamine residues to substrates. UDP-GalNAc is an important building block for the production of glycoproteins and glycolipids in the body. It also serves as a precursor for the synthesis of mucin-type O-glycans, which are important components of mucus and play important roles in biological processes such as cell signaling, immune defense, and lubrication of the digestive tract.

References

↑ Merck Index, 11th Edition, 4240.
1 2 Apte, U. (2014), "Galactosamine", Encyclopedia of Toxicology, Elsevier, pp. 689–690, doi:10.1016/b978-0-12-386454-3.00315-8, ISBN 978-0-12-386455-0 , retrieved 2022-12-08
1 2 Das, Joydeep; Ghosh, Jyotirmoy; Roy, Anandita; Sil, Parames C. (April 2012). "Mangiferin exerts hepatoprotective activity against D-galactosamine induced acute toxicity and oxidative/nitrosative stress via Nrf2–NFκB pathways". Toxicology and Applied Pharmacology. 260 (1): 35–47. doi:10.1016/j.taap.2012.01.015. PMID 22310181.

External links

Galactosamine at the U.S. National Library of Medicine Medical Subject Headings (MeSH)

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[1] Merck Index, 11th Edition, 4240.

[:0-2] 1 2 Apte, U. (2014), "Galactosamine", Encyclopedia of Toxicology, Elsevier, pp. 689–690, doi:10.1016/b978-0-12-386454-3.00315-8, ISBN 978-0-12-386455-0 , retrieved 2022-12-08

[:1-3] 1 2 Das, Joydeep; Ghosh, Jyotirmoy; Roy, Anandita; Sil, Parames C. (April 2012). "Mangiferin exerts hepatoprotective activity against D-galactosamine induced acute toxicity and oxidative/nitrosative stress via Nrf2–NFκB pathways". Toxicology and Applied Pharmacology. 260 (1): 35–47. doi:10.1016/j.taap.2012.01.015. PMID 22310181.

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