Uridine diphosphate N-acetylgalactosamine

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Uridine diphosphate N-acetylgalactosamine
Uridine diphosphate N-acetylgalactosamine or UDP-GalNAc.svg
Names
IUPAC name
Uridine 5′-(2-acetamido-2-deoxy-α-D-galactopyranosyl dihydrogen diphosphate)
Systematic IUPAC name
O1-[(2R,3R,4R,5R,6R)-3-Acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] O3-{[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxyoxolan-2-yl]methyl} dihydrogen diphosphate
Other names
UDP-N-acetylgalactosamine; UDP-GalNAc
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChemSpider
KEGG
PubChem CID
  • InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)
    Key: LFTYTUAZOPRMMI-UHFFFAOYSA-N
  • CC(=O)N[C@@H]1[C@H]([C@H]([C@H](O[C@@H]1OP(=O)(O)OP(=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)CO)O)O
Properties
C17H27N3O17P2
Molar mass 607.355 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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. [1] 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.

See also

Related Research Articles

<i>N</i>-Acetylgalactosamine Chemical compound

N-Acetylgalactosamine (GalNAc), is an amino sugar derivative of galactose.

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

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).

<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.

Uridine diphosphate <i>N</i>-acetylglucosamine Chemical compound

Uridine diphosphate N-acetylglucosamine or UDP-GlcNAc is a nucleotide sugar and a coenzyme in metabolism. It is used by glycosyltransferases to transfer N-acetylglucosamine residues to substrates. D-Glucosamine is made naturally in the form of glucosamine-6-phosphate, and is the biochemical precursor of all nitrogen-containing sugars. To be specific, glucosamine-6-phosphate is synthesized from fructose 6-phosphate and glutamine as the first step of the hexosamine biosynthesis pathway. The end-product of this pathway is UDP-GlcNAc, which is then used for making glycosaminoglycans, proteoglycans, and glycolipids.

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

The enzyme UDP-glucose 4-epimerase, also known as UDP-galactose 4-epimerase or GALE, is a homodimeric epimerase found in bacterial, fungal, plant, and mammalian cells. This enzyme performs the final step in the Leloir pathway of galactose metabolism, catalyzing the reversible conversion of UDP-galactose to UDP-glucose. GALE tightly binds nicotinamide adenine dinucleotide (NAD+), a co-factor required for catalytic activity.

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

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

In enzymology, an UDP-N-acetylgalactosamine-4-sulfate sulfotransferase 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 polypeptide N-acetylgalactosaminyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a N-acetylgalactosamine kinase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">GALNT3</span> Protein-coding gene in the species Homo sapiens

Polypeptide N-acetylgalactosaminyltransferase 3 is an enzyme that in humans is encoded by the GALNT3 gene.

<span class="mw-page-title-main">GALNT1</span> Protein-coding gene in the species Homo sapiens

Polypeptide N-acetylgalactosaminyltransferase 1 is an enzyme that in humans is encoded by the GALNT1 gene.

<span class="mw-page-title-main">GALNT2</span> Protein-coding gene in the species Homo sapiens

Polypeptide N-acetylgalactosaminyltransferase 2 is an enzyme that in humans is encoded by the GALNT2 gene.

<span class="mw-page-title-main">GALNT13</span> Protein-coding gene in the species Homo sapiens

Polypeptide N-acetylgalactosaminyltransferase 13 is an enzyme that in humans is encoded by the GALNT13 gene.

(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

N-acetylneuraminylgalactosylglucosylceramide beta-1,4-N-acetylgalactosaminyltransferase (EC 2.4.1.165, is an enzyme that catalyses the following chemical reaction:

UDP-N-acetylgalactosamine diphosphorylase is an enzyme with systematic name UTP:N-acetyl-alpha-D-galactosamine-1-phosphate uridylyltransferase. This enzyme catalyses the following chemical reaction

Galactosaminogalactan, is an exopolysaccharide composed of galactose and N-acetylgalactosamine (GalNAc). It is commonly found in the biofilm and cell wall of various fungal species. Although the sugar residues are arranged in no particular/discrete order, and thus a heteroglycan, the residues are all linked by α-1,4 glycosidic bonds. Galactosaminogalactan is typically extracted by ethanol precipitation from liquid culture or by alkaline treatment from the cell wall. Once extracted, galactosaminogalactan becomes highly insoluble.

References

  1. ↑ "Uridine-diphosphate-n-acetylgalactosamine". pubchem.ncbi.nlm.nih.gov.
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