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
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
KEGG
UNII
  • 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 checkY
    Key: OVRNDRQMDRJTHS-CBQIKETKSA-N checkY
  • 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
  • O[C@@H](C(CO)O[C@H](O)[C@H]1NC(C)=O)[C@H]1O
Properties
C8H15NO6
Molar mass 221.21 g/mol
Melting point 172 to 173 °C (342 to 343 °F; 445 to 446 K)
Related compounds
N-Acetylglucosamine
Galactosamine
Galactose
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X markN verify (what is checkYX markN ?)

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

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 (3): 437–443. doi:10.1021/bi00891a023.
  2. ↑ 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.