N-Acetylgalactosamine

{{short description|Chemical compound}}

{{DISPLAYTITLE:N-Acetylgalactosamine}}

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| Name =N-Acetylgalactosamine

| ImageFile = N-Acetylgalactosamine Structural Formula V.1.svg

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| IUPACName = 2-(Acetylamino)-2-deoxy-D-galactose

| OtherNames = GalNAc; 2-Acetamido-2-deoxy-D-galactose; N-Acetylchondrosamine; 2-Acetamido-2-deoxy-D-galactopyranose; N-Acetyl-D-galactosamine

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| CASNo = 1811-31-0

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| PubChem = 84265

| SMILES = O[C@@H](C(CO)O[C@H](O)[C@H]1NC(C)=O)[C@H]1O

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| ChemSpiderID = 76020

| 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

| InChIKey = OVRNDRQMDRJTHS-CBQIKETKBW

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| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = OVRNDRQMDRJTHS-CBQIKETKSA-N

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| ChEBI = 40356

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| KEGG = C01074

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| UNII = 833755V695

| DrugBank = DB03567

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| Section2 = {{Chembox Properties

| C=8 | H=15 | N=1 | O=6

| MolarMass = 221.21 g/mol

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| MeltingPtC = 172 to 173

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| Section8 = {{Chembox Related

| OtherFunction = N-Acetylglucosamine
Galactosamine
Galactose

| OtherFunction_label = monosaccharides

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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.{{cite journal |title=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 |author1=Donald M. Marcus |author2=Elvin A. Kabat |author3=Gerald Schiffman |journal=Biochemistry |year=1964 |volume=3 |issue=3 |pages=437–443 |doi=10.1021/bi00891a023 }}

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. {{Cite journal |doi = 10.1021/ja505986a|pmid = 25434769|title = Multivalent N-Acetylgalactosamine-Conjugated siRNA Localizes in Hepatocytes and Elicits Robust RNAi-Mediated Gene Silencing|journal = Journal of the American Chemical Society|volume = 136|issue = 49|pages = 16958–16961|year = 2014|last1 = Nair|first1 = Jayaprakash K|last2 = Willoughby|first2 = Jennifer L. S|last3 = Chan|first3 = Amy|last4 = Charisse|first4 = Klaus|last5 = Alam|first5 = Md. Rowshon|last6 = Wang|first6 = Qianfan|last7 = Hoekstra|first7 = Menno|last8 = Kandasamy|first8 = Pachamuthu|last9 = Kel'In|first9 = Alexander V|last10 = Milstein|first10 = Stuart|last11 = Taneja|first11 = Nate|last12 = o'Shea|first12 = Jonathan|last13 = Shaikh|first13 = Sarfraz|last14 = Zhang|first14 = Ligang|last15 = Van Der Sluis|first15 = Ronald J|last16 = Jung|first16 = Michael E|last17 = Akinc|first17 = Akin|last18 = Hutabarat|first18 = Renta|last19 = Kuchimanchi|first19 = Satya|last20 = Fitzgerald|first20 = Kevin|last21 = Zimmermann|first21 = Tracy|last22 = Van Berkel|first22 = Theo J. C|last23 = Maier|first23 = Martin A|last24 = Rajeev|first24 = Kallanthottathil G|last25 = Manoharan|first25 = Muthiah|url = http://www.escholarship.org/uc/item/54c114pc|url-access = subscription}}

See also

References

{{Reflist}}