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Revision as of 09:01, 10 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi← Previous edit Latest revision as of 02:07, 18 May 2024 edit undo116.98.218.118 (talk)No edit summaryTag: Visual edit 
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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 444023748
| Watchedfields = changed
| ImageFile = Neu5NH2.png
⚫ | verifiedrevid = 444024786
⚫ | ImageSize =
| ImageFile1 = Neuraminic-acid-3D-balls.png | ImageFile = Beta Neuraminic acid.svg
⚫ | ImageSize =
⚫ | IUPACName = (4S,5R,6R,7S,8R)-5-amino-4,6,7,8,9-<br>pentahydroxy-2-oxo-nonanoic acid
| ImageFile1 = Neuraminic-acid-side-based-on-similar-xtals-Mercury-3D-balls.png
⚫ | OtherNames =
| IUPACName = 5-Amino-3,5-dideoxy-{{sm|d}}-''glycero''-{{sm|d}}-''galacto''-non-2-ulosonic acid
⚫ | Section1 = {{Chembox Identifiers
⚫ | OtherNames =
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | SystematicName = (4''S'',5''R'',6''R'',7''S'',8''R'')-5-Amino-4,6,7,8,9-<wbr>pentahydroxy-2-oxononanoic acid
⚫ | Section1 = {{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 447972 | ChemSpiderID = 447972
| InChI = 1/C9H17NO8/c10-5-3(12)1-9(17,8(15)16)18-7(5)6(14)4(13)2-11/h3-7,11-14,17H,1-2,10H2,(H,15,16)/t3-,4+,5+,6+,7+,9-/m0/s1 | InChI = 1/C9H17NO8/c10-5-3(12)1-9(17,8(15)16)18-7(5)6(14)4(13)2-11/h3-7,11-14,17H,1-2,10H2,(H,15,16)/t3-,4+,5+,6+,7+,9-/m0/s1
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CERZMXAJYMMUDR-YOQZMRDMSA-N | StdInChIKey = CERZMXAJYMMUDR-YOQZMRDMSA-N
⚫ | CASNo_Ref = {{cascite|correct|??}}
| CASNo = 114-04-5 | CASNo = 114-04-5
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem = 513472
| UNII = L4866H38XY
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | PubChem = 513472
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 165084
| ChEMBL2_Ref = {{ebicite|changed|EBI}}
| ChEMBL2 = 1234621
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 49022 | ChEBI = 49022
| SMILES = O=C(O)1(O)O((O)(O)CO)(N)(O)C1 | SMILES = O=C(O)1(O)O((O)(O)CO)(N)(O)C1
| MeSHName = Neuraminic+Acids | MeSHName = Neuraminic+Acids
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| Formula = C<sub>9</sub>H<sub>17</sub>N<sub>1</sub>O<sub>8</sub> | Formula = C<sub>9</sub>H<sub>17</sub>NO<sub>8</sub>
| MolarMass = 267.233 g/mol | MolarMass = 267.233 g/mol
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
}} }}
| Section3 = {{Chembox Hazards | Section3 = {{Chembox Hazards
| Solubility = | MainHazards =
| MainHazards = | FlashPt =
| FlashPt = | AutoignitionPt =
| Autoignition =
}} }}
}} }}
] of neuraminic acid in its ] form.]]
⚫ '''Neuraminic acid''' (5-amino-3,5-dideoxy-D-''glycero''-D-''galacto''-non-2-ulosonic acid) is a 9-carbon ], a derivative of a ]. Neuraminic acid may be visualized as the product of an ] product of ] and D-] (2-amino-2-deoxy-mannose). Neuraminic acid does not occur naturally, but many of its derivatives are found widely distributed in animal tissues and in bacteria, especially in ]s and ]s. The ''N''- or ''O''-substituted derivatives of neuraminic acid are collectively known as ]s, the predominant form in mammalian cells being ]. The amino group bears either an acetyl or a glycolyl group. The hydroxyl substituents may vary considerably: Acetyl, lactyl, methyl, sulfate and phosphate groups have been found.
'''Neuraminic acid''' (5-amino-3,5-dideoxy-<small>D</small>-''glycero''-<small>D</small>-''galacto''-non-2-ulosonic acid) is an ] (in particular ]) ] with a backbone formed by nine ]s.<ref name=":0">{{Citation|last=Blanco|first=Antonio|title=Chapter 4 - Carbohydrates|date=2017-01-01|url=http://www.sciencedirect.com/science/article/pii/B9780128035504000045|work=Medical Biochemistry|pages=73–97|editor-last=Blanco|editor-first=Antonio|publisher=Academic Press|language=en|doi=10.1016/b978-0-12-803550-4.00004-5|isbn=978-0-12-803550-4|access-date=2020-12-16|last2=Blanco|first2=Gustavo|editor2-last=Blanco|editor2-first=Gustavo}}</ref> Although 9-carbon sugars do not occur naturally, neuraminic acid may be regarded as a theoretical 9-carbon ] in which the first link of the chain (the –CH<sub>2</sub>OH at ]) is ] into a ] (–C(=O)OH), the ] at position 3 is deoxidised (oxygen is removed from it), and the hydroxyl group at position 5 is substituted with an ] (–NH<sub>2</sub>). Neuraminic acid may also be visualized as the product of an ] of ] and <small>D</small>-] (2-amino-2-deoxy-mannose).<ref name=":0" />


⚫ Neuraminic acid does not occur naturally, but many of its derivatives are found widely distributed in animal tissues and in bacteria, especially in ]s and ]s. The ''N''- or ''O''-substituted derivatives of neuraminic acid are collectively known as ]s, the predominant form in mammalian cells being ]. The amino group bears either an acetyl or a glycolyl group. The hydroxyl substituents may vary considerably: acetyl, lactyl, methyl, sulfate and phosphate groups have been found.
⚫ The name "neuraminic acid" was introduced by German scientist E. Klenk in 1941, in reference to the brain lipids from which it was derived as a cleavage product.<ref>Klenk, E. 1941. Neuraminsäure, das Spaltprodukt eines neuen Gehirnlipoids. ''Zeitschr. f. Physiol. Chem.'' 1941; 268:50-58.</ref>.


⚫ The name "neuraminic acid" was introduced by German scientist E. Klenk in 1941, in reference to the brain lipids from which it was derived as a cleavage product.<ref>Klenk, E. 1941. Neuraminsäure, das Spaltprodukt eines neuen Gehirnlipoids. ''Zeitschr. f. Physiol. Chem.'' 1941; 268:50-58.</ref>
⚫ The symbol commonly used for neuraminic acid is '''Neu''', and the residue is typically found with additional chemical modifications in biological systems. As a family, these residues are known as ]. For example, N-acetyl-neuraminic acid, Neu5Ac, is typical in human glycoproteins.


⚫ The ] symbol used for neuraminic acid is '''Neu''', and the residue is typically found with additional chemical modifications in biological systems. As a family, these residues are known as ]. For example, ''N''-acetylneuraminic acid, Neu5Ac, is typical in human glycoproteins.
⚫ Among their many biological functions, these structures are substrates for ] enzymes which cleave neuraminic acid residues. Human ] viruses have a neuraminidase enzyme, signified in the name "H#N#", where the H refers to an ] of ] and N refers to an isoform of ].

⚫ Among their many biological functions, these structures are substrates for ] enzymes which cleave neuraminic acid residues. Human ] viruses have a neuraminidase enzyme, signified in the name "H#N#", where the H refers to an ] of ] and N refers to an isoform of ].


==See also== ==See also==
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* ] * ]
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* ]


==References and notes== ==References==
{{reflist}} {{reflist}}

{{Carbohydrates}}


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