N-Acetylgalactosamine

N-Acetylgalactosamine
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
PubChem	84265
ChemSpider	76020 Y
Jmol-3D images	Image 1
SMILES O[C@@H](C(CO)O[C@H](O)[C@H]1NC(C)=O)[C@H]1O
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
Properties
Molecular formula	C8H15NO6
Molar mass	221.21 g/mol
Melting point	172-173 °C
Hazards
S-phrases	S24/25
Related compounds
Related monosaccharides	N-Acetylglucosamine Galactosamine Galactose
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

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. http://pubs.acs.org/doi/abs/10.1021/bi00891a023.