Chemistry:N-Acetylgalactosamine

Short description: Chemical compound

N-Acetylgalactosamine

Names
IUPAC name 2-(Acetylamino)-2-deoxy-D-galactose
Other names GalNAc; 2-Acetamido-2-deoxy-D-galactose; N-Acetylchondrosamine; 2-Acetamido-2-deoxy-D-galactopyranose; N-Acetyl-D-galactosamine
Identifiers
CAS Number	1811-31-0 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:40356 Y
ChemSpider	76020 Y
DrugBank	DB03567
KEGG	C01074 Y
PubChem CID	84265
UNII	833755V695 Y
InChI InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6+,7-,8+/m1/s1 Y Key: OVRNDRQMDRJTHS-CBQIKETKSA-N Y InChI=1/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6+,7-,8+/m1/s1 Key: OVRNDRQMDRJTHS-CBQIKETKBW
SMILES O[C@@H](C(CO)O[C@H](O)[C@H]1NC(C)=O)[C@H]1O
Properties
Chemical formula	C8H15NO6
Molar mass	221.21 g/mol
Melting point	172 to 173 °C (342 to 343 °F; 445 to 446 K)
Related compounds
Related monosaccharides	N-Acetylglucosamine Galactosamine Galactose
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Tracking categories (test):

• SizeSet

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

Function

In humans it is the terminal carbohydrate forming the antigen of blood group A.

It is typically the first monosaccharide that connects serine or threonine in particular forms of protein O-glycosylation.

N-Acetylgalactosamine is necessary for intercellular communication, and is concentrated in sensory nerve structures of both humans and animals.

GalNAc is also used as a targeting ligand in investigational antisense oligonucleotides and siRNA therapies targeted to the liver, where it binds to the asialoglycoprotein receptors on hepatocytes.

See also

• Galactosamine
• Globoside
• (N-Acetylglucosamine) GlcNAc