N-Acetylgalactosamine

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	31022-50-1
ChEBI	CHEBI:40356
ChemSpider	76020
Jmol 3D model	Interactive image
PubChem	84265
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 Key: OVRNDRQMDRJTHS-CBQIKETKSA-N 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)
Hazards
S-phrases	S24/25
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

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.^[1]

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.

See also

• Galactosamine
• Globoside
• GlcNAc (N-acetylglucosamine)

References

1. Donald M. Marcus, Elvin A. Kabat, Gerald Schiffman (1964). "Immunochemical Studies on Blood Groups. XXXI. Destruction of Blood Group A Activity by an Enzyme from Clostridium tertium Which Deacetylates N-Acetylgalactosamine in Intact Blood Group Substances". Biochemistry 3: 437–443. doi:10.1021/bi00891a023.