Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and N-Acetylneuraminic acid: Difference between pages

{{DISPLAYTITLE:''N''-Acetylneuraminic acid}}

| Watchedfields = changed

| verifiedrevid = 462257046

| Name =''N''-Acetylneuraminic acid

| ImageFile = Neu5Ac_in_neutral_form%2C_2C5_conformation.png

| ImageName = β anomer

| IUPACName = 5-(Acetylamino)-3,5-dideoxy-<small>D</small>-''glycero''-α-<small>D</small>-''galacto''-non-2-ulopyranosonic acid

| OtherNames = {{ubl

| NANA

| Neu5Ac

| Aceneuramic acid

| Acenobel}}

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 131-48-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = GZP2782OP0

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 61599

| KEGG = D11016

| SMILES = OC(=O)[C@@]1(O)C[C@H](O)[C@@H](NC(C)=O)[C@@H](O1)[C@H](O)[C@H](O)CO

| MeSHName = N-Acetylneuraminic+Acid

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| InChI = 1/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11+/m0/s1

| InChIKey = SQVRNKJHWKZAKO-YRMXFSIDBI

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

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

|Section2={{Chembox Properties

| C=11 | H=19 | N=1 | O=9

| Appearance = White crystalline powder

| Density =

| MeltingPtC = 186

| MeltingPt_notes = (decomposes)

| BoilingPt =

|Section3={{Chembox Pharmacology

| ATCCode_prefix = M09

| ATCCode_suffix = AX05

|Section4={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

'''''N''-Acetylneuraminic acid''' ('''Neu5Ac''' or '''NANA''') is the predominant [[sialic acid]] found in human cells, and many mammalian cells. Other forms, such as [[N-Glycolylneuraminic acid]], may also occur in cells.

This residue is negatively charged at physiological pH and is found in complex [[glycans]] on [[mucin]]s and glycoproteins found at the [[cell membrane]]. Neu5Ac residues are also found in glycolipids, known as [[ganglioside]]s, a crucial component of neuronal membranes found in the [[brain]].

Along with involvement in preventing infections ([[mucus]] associated with [[mucous membrane]]s—mouth, nose, GI, respiratory tract), Neu5Ac acts as a receptor for [[influenza]] viruses, allowing attachment to mucous cells via [[hemagglutinin]] (an early step in acquiring influenzavirus infection).

==In the biology of bacterial pathogens==

Neu5Ac is also important in the biology of a number of pathogenic and symbiotic bacteria<ref name=Severi2006>{{cite journal | vauthors = Severi E, Hood DW, Thomas GH | year = 2007 | title = Sialic acid utilization by bacterial pathogens | journal = Microbiology | volume = 153 | issue = 9| pages = 2817–2822 | pmid = 17768226 | doi=10.1099/mic.0.2007/009480-0| doi-access = free }}</ref><ref>{{Cite journal |last1=Vimr |first1=Eric R. |last2=Kalivoda |first2=Kathryn A. |last3=Deszo |first3=Eric L. |last4=Steenbergen |first4=Susan M. |date=March 2004 |title=Diversity of Microbial Sialic Acid Metabolism |journal=Microbiology and Molecular Biology Reviews |volume=68 |issue=1 |pages=132–153 |doi=10.1128/MMBR.68.1.132-153.2004 |issn=1092-2172 |pmid=15007099|pmc=362108 }}</ref><ref name=Vimr2004>{{cite journal | vauthors = Vimr ER, Kalivoda KA, Deszo EL, Steenbergen SM | year = 2004 | title = Diversity of microbial sialic acid metabolism. | journal = Microbiol Mol Biol Rev | volume = 68 | issue = 1| pages = 132–153 | pmid = 15007099 | pmc=362108 | doi=10.1128/mmbr.68.1.132-153.2004}}</ref> as it can be used either as a nutrient, providing both carbon and nitrogen to the bacteria, or in some pathogens, can be activated and placed on the cell surface.<ref name=Severi2006 /> Bacteria have evolved transporters for Neu5Ac to enable them to capture it from their environment and a number of these have been characterized including the NanT protein from ''[[Escherichia coli]]'',<ref name=Vimr1985>{{cite journal |vauthors = Vimr ER, Troy FA |year = 1985 |title = Identification of an inducible catabolic system for sialic acids (nan) in Escherichia coli |journal = J. Bacteriol. |volume = 164 |issue = 2|pages = 845–853 |doi = 10.1128/jb.164.2.845-853.1985 |pmid = 3902799 |pmc=214328}}</ref> the SiaPQM [[Tripartite ATP-independent periplasmic transporter|TRAP]] transporter from ''[[Haemophilus influenzae]]''<ref name=Severi2005>{{cite journal| vauthors = Severi E, Randle G, Kivlin P, Whitfield K, Young R, Moxon R, Kelly D, Hood D, Thomas GH |year = 2005 |title = Sialic acid transport in Haemophilus influenzae is essential for lipopolysaccharide sialylation and serum resistance and is dependent on a novel tripartite ATP-independent periplasmic transporter|journal = Mol. Microbiol.|volume = 58|issue=4|pages = 1173–1185|pmid = 16262798|doi=10.1111/j.1365-2958.2005.04901.x|s2cid = 32085592 |doi-access = free}}</ref> and the SatABCD [[ABC transporter]] from ''[[Haemophilus ducreyi]]''.<ref name=Post2005>{{cite journal | vauthors = Post DM, Mungur R, Gibson BW, ((Munson RS Jr)) | year = 2005 | title = Identification of a novel sialic acid transporter in Haemophilus ducreyi. | journal = Infect Immun | volume = 73 | issue = 10| pages = 6727–35 | pmid = 16177350 | doi=10.1128/IAI.73.10.6727-6735.2005 | pmc=1230923}}</ref>

==Medical use==

In Japan, Neu5Ac is approved under the trade name Acenobel for the treatment of [[distal myopathy with rimmed vacuoles]].<ref>{{cite web | url = https://www.nobelpharma.co.jp/_cms/wp-content/uploads/2024/03/587fe2db53b3944fb58405e11716b6d1.pdf | title = “ACENOBEL® Sustained Release Tablet 500 mg” Approved for Distal Myopathy with Rimmed Vacuoles | publisher = Nobelpharm }}</ref>

==See also==

* [[Neuraminic acid]]

* [[N-Glycolylneuraminic acid|''N''-Glycolylneuraminic acid]]

* [[Sialic acid]]

== References ==

{{reflist|2}}

{{Other drugs for disorders of the musculo-skeletal system}}

{{Authority control}}

{{DEFAULTSORT:Acetylneuraminic Acid, N-}}

[[Category:Amino sugars]]

[[Category:Sugar acids]]

[[Category:Monosaccharides]]