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
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).
☒N verify (what is checkY☒N ?)
Infobox references

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.

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]

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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.