23755-35-3

Basic information

• Product Name: 2-O-METHYL-ALPHA-D-N-ACETYLNEURAMINIC ACID
• Synonyms: 5-ACETAMIDO-3,5-DIDEOXY-2-ALPHA-O-METHYL-D-GLYCERO-D-GALACTO-2-NONULOSONIC ACID;ALPHA-D-NEU-5-AC-2->OCH3;2-O-Methyl-¤-D-N-acetylneuraminic acid;2-O-Methyl-3-D-N-acetylneuraminicacid;2-O-Methyl-b-D-N-acetylneuraminic Acid;2-O-Methyl-N-acetyl-β-neuraMinic Acid;N-Acetyl-β-neuraMinic Methyl Glycoside
• CAS NO: 23755-35-3
• Molecular Formula: C₁₂H₂₁NO₉
• Molecular Weight: 323.3
• Product Categories: Carbohydrates & Derivatives
• Mol File: 23755-35-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 162-165°C
• Boiling Point: 732.6±60.0 °C(Predicted)
• Appearance: /
• Density: 1.51±0.1 g/cm3(Predicted)
• Storage Temp.: −20°C
• Solubility: Methanol, Water
• PKA: 2.08±0.70(Predicted)
• Stability: Moisture, Temperature sensitive
• CAS DataBase Reference: 2-O-METHYL-ALPHA-D-N-ACETYLNEURAMINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-O-METHYL-ALPHA-D-N-ACETYLNEURAMINIC ACID(23755-35-3)
• EPA Substance Registry System: 2-O-METHYL-ALPHA-D-N-ACETYLNEURAMINIC ACID(23755-35-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 23755-35-3(Hazardous Substances Data)

Usage

Description

2-O-METHYL-ALPHA-D-N-ACETYLNEURAMINIC ACID is a complex organic compound with significant potential in various scientific and medical applications. It is characterized by its off-white powder form and is known for its ability to serve as a model compound for studying the binding of influenza virus hemagglutinin and metal ions.

Uses

Used in Pharmaceutical Research:
2-O-METHYL-ALPHA-D-N-ACETYLNEURAMINIC ACID is used as a model compound for [pharmaceutical research] to [study the binding of influenza virus hemagglutinin and metal ions]. This application is crucial in understanding the mechanisms of viral infections and the development of potential antiviral therapies.
Used in Chemical and Material Science:
In the field of chemical and material science, 2-O-METHYL-ALPHA-D-N-ACETYLNEURAMINIC ACID is used as a [chemical compound] for [exploring its properties and potential applications in various industries]. Its unique structure and properties make it a valuable subject for research and development.
Used in Virology:
2-O-METHYL-ALPHA-D-N-ACETYLNEURAMINIC ACID is used as a [viral research tool] for [investigating the interactions between the influenza virus and host cells]. This knowledge can contribute to the development of new antiviral strategies and treatments for influenza and other viral diseases.
Used in Analytical Chemistry:
In analytical chemistry, 2-O-METHYL-ALPHA-D-N-ACETYLNEURAMINIC ACID is used as a [reference compound] for [calibrating instruments and developing new analytical methods]. Its distinct chemical properties make it a valuable tool for improving the accuracy and reliability of various analytical techniques.
Overall, 2-O-METHYL-ALPHA-D-N-ACETYLNEURAMINIC ACID is a versatile compound with a wide range of applications across different industries, including pharmaceutical research, chemical and material science, virology, and analytical chemistry. Its unique properties and potential for further research make it an important compound to study and utilize in various scientific and medical contexts.

Upstream product

• 73208-80-7 methyl [methyl 4,7,8,9-tetra-O-acetyl-5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-non-2-ulopyranoside]onate 
• 67670-69-3 N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 
• 6931-68-6 methyl (5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 
• 6813-81-6 N-acetyl neuraminic acid 
• 72-87-7 N-acetyl-D-mannosamine 
• 67-56-1 methanol 
• 24967-27-9 2,3-dehydro-2-deoxy-N-acetylneuraminic acid 
• 18409-13-7 3'-sialyllactose 
• 6730-26-3 methyl (methyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 
• 489-46-3 sialic acid 
• 19342-33-7 N-acetyl neuraminic acid 
• 6730-43-4 N-Acetyl-β-D-neuraminylsaeure-methyl-methylglycosid 
• 139932-26-6 (2S,4S,5S,6S)-2-Methoxy-4-phenylcarbamoyloxy-5-trifluoromethanesulfonyloxy-6-((1R,2R)-1,2,3-tris-phenylcarbamoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 139932-27-7 (2S,4S,5R,6R)-5-Azido-2-methoxy-4-phenylcarbamoyloxy-6-((1S,2R)-1,2,3-tris-phenylcarbamoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 

Downstream Products

• 123168-72-9 diphenylmethyl (methyl 5-acetamido-3,5-dideoxy-β-D-galacto-2,8-nondiulopyranosid)onate 
• 123149-46-2 diphenylmethyl onate 
• 123149-45-1 diphenylmethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid)onate 
• 123166-92-7 diphenylmethyl onate 
• 123149-39-3 diphenylmethyl (methyl 5-acetamido-4,8,9-tri-O-acetyl-3,5-dideoxy-β-D-galacto-2,7-nondiulopyranosid)onate 
• 123149-38-2 diphenylmethyl (methyl 5-acetamido-4,8,9-tri-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid)onate 
• 123149-42-8 diphenylmethyl (methyl 5-acetamido-4,7,9-tri-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid)onate 
• 123149-36-0 diphenylmethyl onate 
• 123149-31-5 diphenylmethyl onate 
• 123149-33-7 diphenylmethyl onate 
• 123149-35-9 diphenylmethyl onate 
• 123149-32-6 diphenylmethyl onate 
• 123149-30-4 diphenylmethyl onate 
• 195251-36-6 methyl-5-acetamido-7,8,9-tri-O-benzoyl-3,5-dideoxy-β-D-manno-2-nonulopyranoside-1,4 lactone 

Relevant articles and documents

Semi-Synthetic Sialic Acid Probes for Challenging the Substrate Promiscuity of Enzymes in the Sialoconjugation Pathway

A series of unusual sialic acid analogs were prepared using a semi-synthetic strategy. Truncation of natural N-acetylneuraminic acid was followed by diastereoselective carbon backbone reconstruction using Barbier-type carboligations as well as different functional group interconversions, which provided access to a variety of functional motifs in the terminal carbon backbone, including examples of saturated and unsaturated, linear and branched alkyl chains, partially deoxygenated sialic acids, sialic diacids and a first truncated legionaminic acid analog. The synthetic sialic acid probes were studied for nucleotide activation by the CMP-sialic acid synthetase from Neisseria meningitidis using a universal pH-shift assay for kinetic analysis. One-pot enzymatic nucleotide activation and sialyltransfer to lactose was performed using a selection of five probes together with an engineered α2,3-sialyltransferase from Photobacterium phosphoreum to furnish five new-to-nature analogs of the GM3 trisaccharide, which were finally utilized to test the substrate tolerance of two bacterial sialidases. The obtained set of sialic acid analogs and neo-sialocojugates provides interesting opportunities for further glycobiology studies. (Figure presented.).

SIALIDASE INHIBITORS AND PREPARATION THEREOF

New 2-deoxy-2,3-dehydro-sialic acids and 2,7-anhydro-sialic acids, which are useful as sialidase inhibitors, and enzymatic methods for preparing them are disclosed. The methods include forming a reaction mixture comprising a glycoside acceptor, a sialic acid donor, and a sialyltransferase; maintaining the reaction mixture under conditions sufficient to form a sialoside; and contacting the sialoside with a Streptococcus pneumoniae sialidase to form the sialic acid product. Methods for the inhibition and sialidases and the treatment of cancer and infectious diseases are also disclosed.

CST-II's recognition domain for acceptor substrates in α-(2→8)- sialylations

CST-II is a bacterial sialyltransferase known for its ability to perform α-(2→8)-sialylations using GM3 related trisaccharide substrates. Previously, we probed the enzyme's substrate specificity and developed an efficient synthesis for α-(2→8)-oligosialos