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N-Acetylneuraminic acid Basic information Product Name: N-Acetylneuraminic acid Synonyms: 5-(acetylamino)-3,5-dideoxy-d-glycero-d-galacto-2-nonulosonicaci;LACTAMINIC ACID;5-ACETAMIDO-3,5-DIDEOXY-D-GLYCERO-D-GALACTO-2-NONU;5-ACETAMIDO-3,5-DIDEOXY-D-GLYCERO-D-GALACTO-2-NONULOSONIC ACID;5-ACETAMIDO-3,5-DIDEOXY-D-GLYCERO-D-GALACTO-NONULOPYRANOSONIC ACID HYDRATE;5-ACETAMIDO-3,5-DIDEOXY-D-GLYCERO-D-GALACTONONULOSONIC ACID;5-ACETAMIDO-3,5-DIDEOXY-D-GLYCERO-D-GALACTONULOSONIC ACID;5-ACETYLAMINO-3,5-DIDEOXY-D-GLYCERO-D-GALACTO-2-NONULOSONIC ACID CAS: 131-48-6 MF: C11H19NO9 MW: 309.27 EINECS: 205-023-1 Product Categories: Bioproducts;Sugar derivatives;13C & 2H Sugars;Sialic Acids;Biochemistry;Carbohydrates & Derivatives;Miscellaneous Natural Products;Zanamavir;Sugar Acids;Sugars;Miscellaneous Compounds;carbohydrate;API Mol File: 131-48-6.mol   N-Acetylneuraminic acid Chemical Properties Melting point  184-186 °C alpha  -32 º (c=2,water) Boiling point  449.56°C (rough estimate) density  1.3580 (rough estimate) refractive index  -32 ° (C=1, H2O) storage temp.  -20°C solubility  50 g/L (20°C) pka 2.41±0.54(Predicted) form  synthetic, crystalline color  White to Off-White Water Solubility  50 g/L (20 ºC) Sensitive  Air Sensitive Merck  14,8484 BRN  1716283 Stability: Stable. Incompatible with strong oxidizing agents. InChIKey SQVRNKJHWKZAKO-PFQGKNLYSA-N CAS DataBase Reference 131-48-6(CAS DataBase Reference) EPA Substance Registry System Neuraminic acid, N-acetyl- (131-48-6)   Safety Information Hazard Codes  Xi Risk Statements  36/37/38 Safety Statements  22-24/25-36-26 WGK Germany  3 F  3-10-23 Hazard Note  Irritant TSCA  Yes HS Code  29329970 MSDS Information Provider Language o-Sialic acid English SigmaAldrich English ACROS English ALFA English   N-Acetylneuraminic acid Usage And Synthesis Chemical Properties N-acetylneuraminic acid is an N-acyl derivative of neuraminic or acid amino sugar derivative, derived from N-acetylmannosamine and pyruvic acid. It is an important constituent of glycoproteins and glycolipids. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. Physical properties The numbering of the sialic acid structure begins at the carboxylate carbon and continues around the chain. The configuration which places the carboxylate in the axial position is the alpha-anomer. The alpha-anomer is the form that is found when sialic acid is bound to glycans, however, in solution it is mainly (over 90 %) in the beta-anomeric form. A bacterial enzyme with sialic acid mutarotase activity, NanM, has been discovered which is able to rapidly equilibrate solutions of sialic acid to the resting equilibrium position of around 90 % beta 10 % alpha. Uses Carbon 13 labelled analogue of N-Acetylneuraminic acid (A187000). N-Acetylneuraminic acid is useful biologically in neurotransmission, leukocyte extravasation, viral or bacterial infections and carbohydrate-protein recognition. Neu5Ac is used to study its biochemistry, metabolism and uptake in vivo and in vitro. Neu5Ac is used in the development of nanocarriers. Uses N-Acetylneuraminic acid (NANA, Neu5Ac) is a major component of glycoconjugates such as glycolipids, glycoproteins and proteoglycans (sialogylcoproteins) where it confers selective binding characteristics to the glycosylated component. Neu5Ac is used to study its biochemistry, metabolism and uptake in vivo and in vitro. Neu5Ac is used in the development of nanocarriers. Definition ChEBI: N-acetylneuraminic acid is an N-acylneuraminic acid where the N-acyl group is specified as acetyl. It has a role as an antioxidant, an EC 3.2.1.18 (exo-alpha-sialidase) inhibitor, a bacterial metabolite, a human metabolite and a mouse metabolite. It is a conjugate acid of a N-acetylneuraminate. Biosynthesis In bacterial systems, sialic acids are biosynthesized by an aldolase enzyme. The enzyme uses a mannose derivative as a substrate, inserting three carbons from pyruvate into the resulting sialic acid structure. These enzymes can be used for chemoenzymatic synthesis of sialic acid derivatives. Biological Functions Sialic acid-rich glycoproteins (sialoglycoproteins) bind selectin in humans and other organisms. Metastatic cancer cells often express a high density of sialic acid-rich glycoproteins. This overexpression of sialic acid on surfaces creates a negative charge on cell membranes. This creates repulsion between cells (cell opposition) and helps these late-stage cancer cells enter the blood stream. Sialic acid also plays an important role in human influenza infections. Many bacteria also use sialic acid in their biology, although this is usually limited to bacteria that live in association with higher animals (deuterostomes). Many of these incorporate sialic acid into cell surface features like their lipopolysaccharide and capsule, which helps them evade the innate immune response of the host.[6] Other bacteria simply use sialic acid as a good nutrient source, as it contains both carbon and nitrogen and can be converted to fructose-6- phosphate, which can then enter central metabolism. Sialic acid-rich oligo saccharides on the glyco conjugates ( glyco lipids, glyco proteins, proteoglycans) found on surface membranes help keep water at the surface of cells . The sialic acid - rich regions contribute to creating a negative charge on the cells' surfaces. Since water is a polar molecule with partial positive charges on both hydrogen atoms, it is attracted to cell surfaces and membranes. This also contributes to cellular fluid uptake. Sialic acid can "hide" mannose antigens on the surface of host cells or bacteria from mannose - binding lectin . This prevents activation of complement. Sialic acid in the form of poly sialic acid is an unusual posttranslational modification that occurs on the neural cell adhesion molecules (NCAMs). In the synapse, the strong negative charge of the polysialic acid prevents NCAM cross-linking of cells. Biochem/physiol Actions Both sialic acid and neuraminic acid are loosely used to refer to conjugates of neuraminic acid. N-Acetylneuraminic acid is often found as the terminal sugar of cell surface glycoproteins. Cell surface glycoproteins have important roles in cell recognition and interaction as well as in cell adhesion. Membrane glycoproteins are also important in tumor growth and metastases.   N-Acetylneuraminic acid Preparation Products And Raw materials

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Leader Biochemical Group is a large leader incorporated industry manufacturers and suppliers of advanced refined raw materials From the year of 1996 when our factory was put into production to year of 2020, our group has successively invested in more than 52 factories with shares and subordinates.We focus on manufacture Pharm & chemicals, functional active ingredients, nutritional Ingredients, health care products, cosmetics, pharmaceutical and refined feed, oil, natural plant ingredients industries to provide top quality of GMP standards products.All the invested factories' product lines cover API and intermediates, vitamins, amino acids, plant extracts, daily chemical products, cosmetics raw materials, nutrition and health care products, food additives, feed additives, essential oil products, fine chemical products and agricultural chemical raw materials And flavors and fragrances. Especially in the field of vitamins, amino acids, pharmaceutical raw materials and cosmetic raw materials, we have more than 20 years of production and sales experience. All products meet the requirements of high international export standards and have been recognized by customers all over the world. Our manufacture basement & R&D center located in National Aerospace Economic & Technical Development Zone Xi`an Shaanxi China. Now not only relying on self-cultivation and development as well as maintains good cooperative relations with many famous research institutes and universities in China. Now, we have closely cooperation with Shanghai Institute of Organic Chemistry of Chinese Academy of Science, Beijing Institute of Material Medical of Chinese Academy of Medical Science, China Pharmaceutical University, Zhejiang University. Closely cooperation with them not only integrating Science and technology resources, but also increasing the R&D speed and improving our R&D power. Offering Powerful Tech supporting Platform for group development. Keep serve the manufacture and the market as the R&D central task, focus on the technical research.  Now there are 3 technology R & D platforms including biological extract, microorganism fermentation and chemical synthesis, and can independently research and develop kinds of difficult APIs and pharmaceutical intermediates. With the strong support of China State Institute of Pharmaceutical Industry (hereinafter short for CSIPI), earlier known as Shanghai Institute of Pharmaceutical Industry (SIPI), we have unique advantages in the R & D and industrialization of high-grade, precision and advanced products.  Now our Group technical force is abundant, existing staff more that 1000 people, senior professional and technical staff accounted for more than 50% of the total number of employees, including 15 PhD research and development personnel, 5 master′ S degree in technical and management personnel 9 people. We have advanced equipment like fermentation equipment and technology also extraction, isolation, purification, synthesis with rich production experience and strict quality control system, According to the GMP required, quickly transforming the R&D results to industrial production in time, it is our advantages and our products are exported to North and South America, Europe, Middle East, Africa, and other five continents and scale the forefront in the nation, won good international reputation.  We believe only good quality can bring good cooperation, quality is our key spirit during our production, we are warmly welcome clients and partner from all over the world contact us for everlasting cooperation, Leader will be your strong, sincere and reliable partner in China.

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