33993-25-8

Usage

Uses

Used in Chemical and Pharmaceutical Industry:
2-Naphthyl-beta-D-galactopyranoside is used as a substrate for the detection and quantification of galactosidases, which are enzymes that catalyze the hydrolysis of galactosides. This application is particularly important in the study of enzyme kinetics, enzyme inhibition, and the development of new drugs targeting these enzymes.
Used in Research and Development:
In the field of research and development, 2-Naphthyl-beta-D-galactopyranoside is used as a model compound for studying the interactions between carbohydrates and proteins. This is crucial for understanding the molecular mechanisms of various biological processes, such as cell adhesion, cell signaling, and immune response.
Used in Analytical Chemistry:
2-Naphthyl-beta-D-galactopyranoside is employed as a reference compound in the development and validation of analytical methods for the detection and quantification of carbohydrates. Its unique chemical properties make it an ideal candidate for the calibration of instruments and the establishment of standard curves in various analytical techniques.
Used in Material Science:
In material science, 2-Naphthyl-beta-D-galactopyranoside can be used as a building block for the synthesis of novel carbohydrate-based materials with potential applications in areas such as drug delivery, sensors, and biocompatible coatings.
Used in Biotechnology:
2-Naphthyl-beta-D-galactopyranoside is utilized as a reporter molecule in the field of biotechnology, particularly in the development of biosensors and the study of enzyme activity. Its ability to produce a colorimetric or fluorescent signal upon interaction with specific enzymes makes it a valuable tool for monitoring enzymatic reactions in real-time.

Upstream product

• 135-19-3 β-naphthol 
• 4163-60-4 β-D-galactose peracetate 
• 108-24-7 acetic anhydride 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 875-83-2 sodium 2-naphtholate 

Relevant academic research and scientific papers

Hierarchical Self-Assembly of a Water-Soluble Organoplatinum(II) Metallacycle into Well-Defined Nanostructures

A water-soluble metallosupramolecular hexagon containing pendant methyl viologen (MV) and trimethylammonium units at the vertices has been synthesized via an organoplatinum(II) pyridyl coordination-driven self-assembly reaction. The MV units of the metallacycle were further utilized in the formation of a heteroternary complex with cucurbit[8]uril and a galactose-functionalized naphthalene derivative, yielding a metallacycle-cored carbohydrate cluster that was subsequently ordered into nanospheres and tapes, depending upon the concentration.

Structure-based discovery of glycomimetic FmlH ligands as inhibitors of bacterial adhesion during urinary tract infection

Treatment of bacterial infections is becoming a serious clinical challenge due to the global dissemination of multidrug antibiotic resistance, necessitating the search for alternative treatments to disarm the virulence mechanisms underlying these infections. Uropathogenic Escherichia coli (UPEC) employs multiple chaperone- usher pathway pili tipped with adhesins with diverse receptor specificities to colonize various host tissues and habitats. For example, UPEC F9 pili specifically bind galactose or N-acetylgalactosamine epitopes on the kidney and inflamed bladder. Using X-ray structureguided methods, virtual screening, and multiplex ELISA arrays, we rationally designed aryl galactosides and N-acetylgalactosaminosides that inhibit the F9 pilus adhesin FmlH. The lead compound, 29β-NAc, is a biphenyl N-acetyl-β-galactosaminoside with a Ki of ～90 nM, representing a major advancement in potency relative to the characteristically weak nature of most carbohydrate-lectin interactions. 29β-NAc binds tightly to FmlH by engaging the residues Y46 through edge-to-face π-stacking with its A-phenyl ring, R142 in a salt-bridge interaction with its carboxylate group, and K132 through watermediated hydrogen bonding with its N-acetyl group. Administration of 29β-NAc in a mouse urinary tract infection (UTI) model significantly reduced bladder and kidney bacterial burdens, and coadministration of 29β-NAc and mannoside 4Z269, which targets the type 1 pilus adhesin FimH, resulted in greater elimination of bacteria from the urinary tract than either compound alone. Moreover, FmlH specifically binds healthy human kidney tissue in a 29β-NAc-inhibitable manner, suggesting a key role for F9 pili in human kidney colonization. Thus, these glycoside antagonists of FmlH represent a rational antivirulence strategy for UPEC-mediated UTI treatment.

Solution and Solid-Phase Stereocontrolled Synthesis of 1,2-cis-Glycopyranosides with Minimally Protected Glycopyranosyl Donors Catalyzed by BF3-N,N-Dimethylformamide Complex

Methods are described for the stereoselective synthesis of 1,2-cis glycopyranosides in the d-galacto, d-gluco, and 2-azido-2-deoxy-d-glucopyranoside series utilizing minimally protected (3-bromo-2-pyridyloxy) β-d-glycopyranosyl donors in the presence of BF3-N,N-dimethylformamide (DMF) as a catalyst and a variety of alcohol acceptors relying on the "remote activation concept". Precursors to antifreeze glycopeptide components are synthesized in excellent yields and high α/β ratios. The method is adaptable to one-pot sequential glycosidation as well as to solid-supported synthesis giving access to diverse sets of minimally protected α-d-glycopyranosides as major products.