Neuraminic acid (from the Greek. Νεύρο - vein, nerve and English amino - amino group -NH 2 ) - a natural compound, carbohydrate , 5-amino-3,5-dideoxy-D- glycero -D- galacto- nonulosonic acid - is a ketononose derivative [1] containing 9 carbon atoms. The ketone group is located next to the carboxylic acid, forming the base - nonulosonic acid. In the latter, in the 3rd position, the hydroxyl group is replaced by a hydrogen atom, and in the 5th, by an amino group [2] .
| Neuraminic acid | |
|---|---|
  | |
| Are common | |
| Systematic name | (4S, 5R, 6R, 7S, 8R) -5-amino-4,6,7,8,9-pentohydroxy-2-oxo-nonanoic acid, 3,5-dideoxy-5-aminononulosonic acid |
| Traditional names | neuraminic acid |
| Chem. formula | C 9 H 17 NO 8 |
| Physical properties | |
| condition | solid. |
| Molar mass | 267.2332 ± 0.011 g / mol |
| Thermal properties | |
| T. melt. | 184–186 ° C |
| Classification | |
| Reg. CAS number | 114-04-5 |
| PubChem | |
| Smiles | |
| Inchi | |
| Chebi | 7539 |
| ChemSpider | |
Neuraminic acid is found in nature in a free state only in cerebrospinal fluid [2] , but many of its derivatives are widely distributed in the tissues of animals and bacteria, especially as part of glycoproteins and gangliosides . As a structural component, it is part of the oligosaccharides of milk , mucopolysaccharides , etc. [3] . N- or O-substituted derivatives of neuraminic acid are known collectively as sialic acids , the predominant form in mammalian cells is usually N-acetylneuraminic acid .
The name “neuraminic acid” was introduced by the German scientist E. Klenk in 1941 [4] . It is named after the lipid contained in the brain , from which it was isolated as a hydrolysis product.
The biosynthesis of neuraminic acid proceeds with the participation of derivatives of hexosamines and pyruvic acid .
In some pathological conditions ( cancer , tuberculosis , mental illness , the active phase of rheumatism [5] ), the content of neuraminic acid in body fluids and tissues increases sharply. Neuraminic acid in the composition of glycolipids is involved in the binding of certain viruses and neurotoxins in animal organisms. Mucoproteins containing neuraminic acid play a role in various immune responses , in particular with the influenza virus [3] . The destruction of neuraminidase neuraminic acid, which is part of the surface receptors of mucous membrane cells , facilitates the penetration of microbes into the tissue [1] .
Notes
- ↑ 1 2 Neuraminic acid (neuram . Date of treatment March 24, 2013. Archived on April 9, 2013.
- ↑ 1 2 Tyukavkina N. A., Baukov Yu. I. Bioorganic chemistry: Textbook. - 2nd ed., Revised. and add. - M.: Medicine, 1991. - 528 pp., Ill. - (Textbook. Lit. For student medical. In-to). - ISBN 5-225-00863-1
- ↑ 1 2 XuMuK.ru - Aminosugar . Date of treatment March 24, 2013. Archived on April 9, 2013.
- ↑ Klenk, E. 1941. Neuraminsäure, das Spaltprodukt eines neuen Gehirnlipoids. Zeitschr. f. Physiol. Chem. 1941; 268: 50-58.
- ↑ MOH: Medicine and Health »Research in rheumatology» Neuraminic (sialic) acid . Date of treatment October 24, 2018. Archived on April 9, 2013.
See also
- Sialic acids
- N-acetylneuraminic acid