21698-14-6

Basic information

• Product Name: 2-(β-D-galactosyloxy)ethyl methacrylate
• CAS NO: 21698-14-6
• Molecular Weight: 292.286
• Mol File: 21698-14-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 490.3±45.0 °C(Predicted)
• Density: 1.37±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2-(β-D-galactosyloxy)ethyl methacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(β-D-galactosyloxy)ethyl methacrylate(21698-14-6)
• EPA Substance Registry System: 2-(β-D-galactosyloxy)ethyl methacrylate(21698-14-6)

Safety Data

• Hazardous Substances Data: 21698-14-6(Hazardous Substances Data)

Usage

Molecular Structure

A methacrylate-based compound with a galactose side chain.

Synthesis

Derived from methacrylate.

Applications

Widely used in the synthesis of glycopolymer-based materials.

Uses

Has applications in drug delivery, tissue engineering, and biomaterials.

Mechanism

The presence of the galactose group in GEMA allows for targeted drug delivery systems, as it can specifically bind to galactose-receptor proteins on the surface of cells.

Properties

GEMA can be polymerized to form hydrogels with controlled release properties, making it a valuable component in the development of advanced materials for biomedical applications.

Upstream product

• 868-77-9 2-methyl-2-propenoic acid 2-hydroxyethyl ester 
• 1190202-85-7 but-2-yn-1-yl β-D-galactopyranoside 
• 151168-59-1 1-propynyl-β-D-galactopyranoside 
• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 7296-64-2 β-D-galactopyranoside 
• 74808-10-9 O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)trichloroacetimidate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 47703-15-1 2-O-((2',3',4',6'-tetra-O-acetyl)-β-D-galactosyl)hydroxyethyl methacrylate 

Relevant articles and documents

Enzymatic Synthesis of 2-(β-Galactosyl)-ethyl Methacrylate by β-Galactosidase from Pyrococcus woesei and Application for Glycopolymer Synthesis and Lectin Studies

Glycosidases have long been used for the synthesis of glycosides by transglycosylation reactions. Especially glycosidases from hyperthermophilic bacteria are useful for reactions under extreme reaction conditions, e.g., in the presence of organic solvents. We herein report the facile enzymatic synthesis and purification of 2-(β-galactosyl)-ethyl methacrylate (Gal-EMA) with the recombinant hyperthermostable glycosidase from Pyrococcus woesei in high yields. Optimized reaction conditions resulted in gram-scale synthesis of the galactosylated monomer with 88% transglycosylation yield. The product Gal-EMA was characterized by high-performance liquid chromatography-electrospray ionization-mass spectrometry (HPLC-ESI-MS), nuclear magnetic resonance (NMR) spectroscopy, and infrared (IR) spectroscopy. Gal-EMA was utilized to synthesize sugar-functionalized acrylate polymers with defined amounts of incorporated galactose (0-100%). Analysis of the binding affinity of the lectin RCA120 from Ricinus communis to the glycopolymers using an enzyme-linked lectin assay (ELLA) revealed KD values between 0.24 and 6.2 nM, depending on the amount of incorporated Gal-EMA. The potential of Gal-EMA for the synthesis of acrylate-functionalized glycan oligomers was demonstrated by sequential elongation of the terminal galactose by two glycosyltransferases, resulting in the terminal glycan N-acetyllactosamine (LacNAc) epitope. In conclusion, the enzymatic synthesis of Gal-EMA opens new routes to a series of novel monomeric building blocks for the synthesis of glycan-functionalized polyacrylates.

Glycosylation using unprotected alkynyl donors

(Chemical Equation Presented) Gold(III) activation of unprotected propargyl glycosyl donors has been shown to be effective for the synthesis of saccharides. Terminal propargyl glycosides of glucose, galactose, and mannose required heating at reflux in ace

Investigation of the interaction between peanut agglutinin and synthetic glycopolymeric multivalent ligands

The interaction between synthetic glycoplymers bearing β-D-galactose side groups and the lectin peanut agglutinin (PNA) was investigated by UV-difference spectroscopy and isothermal titration calorimetry (ITC). UV-difference spectroscopy indicated that the polymer-lectin interaction was stronger than that between PNA and either the corresponding monomer, D-galactose or D-lactose. The thermodynamics of binding (K, ΔG, ΔH, ΔS and n) were determined from ITC data by fitting with a two-site, non-cooperative binding model. It was found that the glycopolymer displayed around a 50 times greater affinity for the lectin than the parent carbohydrate, and around 10 times greater than the monomer, on a valency-corrected basis. Binding was found to be entropically driven, and was accompanied by aggregation and precipitation of protein molecules. Furthermore, interesting differences between polymers prepared either from deacetylated monomers, or by deacetylation of pre-formed polymers, were found. The Royal Society of Chemistry 2005.