N-Acetylgalactosamine

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

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
CompTox Dashboard (EPA)	DTXSID70884733
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). N verify (what is ^YN ?) Infobox references

Function edit

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.

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. ^[2]

^ 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 (3): 437–443. doi:10.1021/bi00891a023.
^ Nair, Jayaprakash K; Willoughby, Jennifer L. S; Chan, Amy; Charisse, Klaus; Alam, Md. Rowshon; Wang, Qianfan; Hoekstra, Menno; Kandasamy, Pachamuthu; Kel'In, Alexander V; Milstein, Stuart; Taneja, Nate; o'Shea, Jonathan; Shaikh, Sarfraz; Zhang, Ligang; Van Der Sluis, Ronald J; Jung, Michael E; Akinc, Akin; Hutabarat, Renta; Kuchimanchi, Satya; Fitzgerald, Kevin; Zimmermann, Tracy; Van Berkel, Theo J. C; Maier, Martin A; Rajeev, Kallanthottathil G; Manoharan, Muthiah (2014). "Multivalent N-Acetylgalactosamine-Conjugated siRNA Localizes in Hepatocytes and Elicits Robust RNAi-Mediated Gene Silencing". Journal of the American Chemical Society. 136 (49): 16958–16961. doi:10.1021/ja505986a. PMID 25434769.