Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound
Two-dimensional representation of neuraminic acid in its straight chain form.
Neuraminic acid (5-amino-3,5-dideoxy-D-glycero-D-galacto-non-2-ulosonic acid) is an acidic (in particular ulosonic) amino sugar with a backbone formed by nine carbon atoms.[1] Although 9-carbon sugars do not occur naturally, neuraminic acid may be regarded as a theoretical 9-carbon ketose in which the first link of the chain (the –CH2OH at position 1) is oxidised into a carboxyl group (–C(=O)OH), the hydroxyl group at position 3 is deoxidised (oxygen is removed from it), and the hydroxyl group at position 5 is substituted with an amino group (–NH2). Neuraminic acid may also be visualized as the product of an aldol-condensation of pyruvic acid and D-mannosamine (2-amino-2-deoxy-mannose).[1]
Neuraminic acid does not occur naturally, but many of its derivatives are found widely distributed in animal tissues and in bacteria, especially in glycoproteins and gangliosides. The N- or O-substituted derivatives of neuraminic acid are collectively known as sialic acids, the predominant form in mammalian cells being N-acetylneuraminic acid. 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.[2]
The IUPAC 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 sialic acids. For example, N-acetylneuraminic acid, Neu5Ac, is typical in human glycoproteins.
Among their many biological functions, these structures are substrates for neuraminidase enzymes which cleave neuraminic acid residues. Human flu viruses have a neuraminidase enzyme, signified in the name "H#N#", where the H refers to an isoform of hemagglutinin and N refers to an isoform of viral neuraminidase.
^ abBlanco, Antonio; Blanco, Gustavo (2017-01-01), Blanco, Antonio; Blanco, Gustavo (eds.), "Chapter 4 - Carbohydrates", Medical Biochemistry, Academic Press, pp. 73–97, doi:10.1016/b978-0-12-803550-4.00004-5, ISBN 978-0-12-803550-4, retrieved 2020-12-16
^Klenk, E. 1941. Neuraminsäure, das Spaltprodukt eines neuen Gehirnlipoids. Zeitschr. f. Physiol. Chem. 1941; 268:50-58.
Neuraminicacid (5-amino-3,5-dideoxy-D-glycero-D-galacto-non-2-ulosonic acid) is an acidic (in particular ulosonic) amino sugar with a backbone formed...
synaptogenesis. More than 50 kinds of sialic acid are known, all of which can be obtained from a molecule of neuraminicacid by substituting its amino group or...
N-linked glycosylation or O-linked glycosylation of the proteoglycan Hyaluronic acid (also known as hyaluronan), which is synthesized by integral membrane synthases...
basis for KDO) Nonoses: D-glycero-D-galacto-nonulose (the basis for neuraminicacid) Lindhorst, Thisbe K. (2007). Essentials of Carbohydrate Chemistry...
other nutrients and chemicals are absorbed. Soluble fiber binds to bile acids in the small intestine, making them less likely to enter the body; this...
mirror image l-2-deoxyribose. d-2-deoxyribose is a precursor to the nucleic acid DNA. 2-deoxyribose is an aldopentose, that is, a monosaccharide with five...
in Benedict's reagent. In such a reaction, the sugar becomes a carboxylic acid. All monosaccharides are reducing sugars, along with some disaccharides,...
sialoglycoconjugates, sulfated glycolipids, glycoproteins, fibronectin, and neuraminicacid receptors. Lectins on the surface of the bacterial cells are capable...
glycans: oligosaccharide chains are linked to lipids or to compatible amino acid side chains in proteins, by N- or O-glycosidic bonds. N-Linked oligosaccharides...
glycosidic linkages of neuraminicacids: Hydrolysis of α-(2→3)-, α-(2→6)-, α-(2→8)- glycosidic linkages of terminal sialic acid residues in oligosaccharides...
C1 in the saccharide. Pharmacologists often join substances to glucuronic acid via glycosidic bonds in order to increase their water solubility; this is...
where X is any amino acid except proline and the glycan may be composed of N-acetylgalactosamine, galactose, neuraminicacid, N-acetylglucosamine, fucose...
can ferment FOS, which results in a reduced pH. Calcium is more soluble in acid, and, therefore, more of it comes out of food and is available to move from...
during malting and mashing in beer brewing or by applying dry heat under acidic conditions (pyrolysis or roasting). This procedure was first discovered...
can bind with another hydrophobic guest molecule such as iodine, a fatty acid, or an aromatic compound. This is known as the V form and is how amylopectin...
glyceraldehyde-3-phosphate and dihydroxyacetone phosphate. Lactic acid and pyruvic acid are later derived from these molecules. Importance of Triose in...
contain neuraminicacid, a sugar with an acidic carboxy-group. However, some globosides with the core structure Cer-Glc-Gal-Gal do contain neuraminicacid, e...
the colon by bacterial flora into short-chain fatty acids, including lactic acid and acetic acid. These partially dissociate, acidifying the colonic contents...
found in the enzyme preparation, and no match was found in the enzyme amino acid sequence with those of known allergens. Allulose was first discovered in...
and fouls plumbing. Dextran is now produced from sucrose by certain lactic acid bacteria of the family lactobacillus. Species include Leuconostoc mesenteroides...
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