5094-33-7

Usage

Uses

Used in Molecular Biology and Biotechnology:
4-AMINOPHENYL-BETA-D-GALACTOPYRANOSIDE is used as a substrate in the development of β-galactosidase (GUS)-dependent assay systems for the detection and quantification of β-galactosidase activity. This application is crucial in various research and diagnostic processes, as it allows for the monitoring of gene expression and enzyme activity.
Used in Affinity Matrices Creation:
4-AMINOPHENYL-BETA-D-GALACTOPYRANOSIDE is also used in the creation of affinity matrices for the capture or purification of β-galactosidase enzymes. This application is vital in the field of protein purification, as it enables the isolation of specific enzymes for further study or use in various biotechnological and pharmaceutical applications.

InChI:InChI=1/C12H17NO6/c13-6-1-3-7(4-2-6)18-12-11(17)10(16)9(15)8(5-14)19-12/h1-4,8-12,14-17H,5,13H2/t8-,9+,10+,11-,12-/m1/s1

Upstream product

• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 
• 17042-39-6 p-nitrophenyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 
• 2872-66-4 4-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 86520-63-0 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 25878-60-8 D-galactose pentaacetate 
• 42011-36-9 (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-aminophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 4163-60-4 β-D-galactose peracetate 
• 100-02-7 4-nitro-phenol 

Downstream Products

• 58130-70-4 C₄₂H₄₈N₆O₂₁ 
• 1425814-78-3 C₂₈H₃₉ClN₂O₁₀ 
• 1415663-16-9 C₃₄H₅₁N₃O₁₀ 
• 1415663-13-6 C₂₈H₄₀N₂O₉ 
• 1415663-14-7 C₂₂H₂₈N₂O₉ 
• 7296-64-2 β-D-galactopyranoside 
• 123-30-8 4-amino-phenol 
• 170940-41-7 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acetylamino-phenoxy)-tetrahydro-pyran-3-yl ester 
• 20581-47-9 p-(bromoacetamide)phenyl β-D-galactopyranoside 

Relevant academic research and scientific papers

Targeted delivery of siRNA to hepatocytes and hepatic stellate cells by bioconjugation

Previously, we successfully conjugated galactosylated poly(ethylene glycol) (Gal-PEG) to oligonucleotides (ODNs) via an acid labile ester linker (Zhu et al., Bioconjugate Chem. 2008, 19, 290-8). In this study, sense strands of siRNA were conjugated to Gal

Enzymatic Synthesis of a Series of Thioglycosides: Analogs of Arbutin with Efficient Antipigmentation Properties

Arbutin, a natural glycoside, is well known as a commercial tyrosinase inhibitor, and thus, to prevent pigmentary disorders of skin. In fact, tyrosinase is involved in the biosynthesis of melanin, the skin main pigment. However, arbutin is subject to hydr

An Improved Protocol for the Synthesis and Purification of Yariv Reagents

Yariv reagents are glycoconjugate tris-azo dyes widely used in plant biology. These reagents are synthesized by diazo coupling between phloroglucinol and a para-diazophenyl glycoside. Despite their synthetic accessibility, well-defined protocols for obtai

CARBOHYDRATE FUNCTIONALISED SURFACES

Carbohydrates are biomolecules that are involved in a range of biological processes and play key roles in, for instance, host immune response and cellular adhesion. Accordingly, functionalisation of medical devices such as stents, valves, catheters, prostheses and other devices for in vivoimplantation with carbohydrates is an area in which considerable interest is developing. Disclosed herein are surfaces having carbohydrates immobilised thereon. The carbohydrate has a linker moiety covalently bound thereto and the linker moiety has a carbon atom that forms a covalent bond with an atom on the target surface. The carbon based bond is a strong, non-hydrolysable covalent bond. Diazonium salts are utilised to produce the functionalised surfaces and they are particularly advantageous as they result in non-toxic readily escapable by-products

Carbohydrate coatings via aryldiazonium chemistry for surface biomimicry

Carbohydrates are extremely important biomolecules and their immobilization onto solid surfaces is of interest for the development of new biomimetic materials and of new methods for understanding processes in glycobiology. We have developed an efficient surface modification methodology for the functionalization of a range of materials with biologically active carbohydrates based on aryldiazonium chemistry. We describe the synthesis and characterization of carbohydrate reagents, which were subsequently employed for the one-step, solution-based modification of carbon, metals, and alloys with monosaccharides. We used a combination of spectroscopic and nanogravimetric methods to characterize the structure of the carbohydrate layers; we report an average surface coverage of 7.8 × 10-10 mol cm-2 under our experimental conditions. Concanavalin A, a mannose-binding lectin, and Peanut Agglutinin, a galactose-binding lectin, were found to bind from solution to their respective monosaccharide binding partners immobilized at the surface. This result suggests that the spontaneous chemisorption of aryldiazonium monosaccharide precursors leads to the formation of monosaccharide layers that retain the biological recognition specificity of the parent carbohydrate molecule. Finally, we carried out measurements using fluorescently labeled Bovine Serum Albumin (BSA) and found that these carbohydrate coatings reduce unspecific adsorption of this protein at carbon surfaces. These results suggest that aryldiazonium-derived carbohydrate coatings may offer a promising strategy for preventing undesirable protein accumulation onto surfaces.

Synthesis and biodistribution studies of carbohydrate derivatives radiolabeled with technetium-99m

Three carbohydrate derivatives, MAG3-Gl, MAG3-Ga, MAG3-NG, were synthesized and radiolabeled in high yields. These substances were injected in health Swiss mice and their biodistribution were evaluated. Among them, 99

Self-assembling structures of long-chain sugar-based amphiphiles influenced by the introduction of double bonds

Nine phenyl glucoside or galactoside amphiphiles possessing a saturated or unsaturated long alkyl-chain group as the self-assembling unit of a highly organized molecular architecture were synthesized. Their self-assembly properties were investigated by using energy-filtering TEM (EF-TEM), SEM, CD, XRD, and FT-IR techniques. Compound 2, possessing one cis double bond in the lipophilic portion, exhibited twisted helical fibers, which formed a bilayered structure with a 3.59 nm period, while 3 exhibited helical ribbons and left-handed nanotubu-lar structures with 150-200 nm inner diameters and a wall thickness of approximately 20 nm. Very interestingly, 4, possessing three cis double bonds, exhibited a nanotubular structure with an inner diameter of approximately 70 nm and a d spacing value of 4.62 nm. On the other hand, 7, possessing two trans double bonds in the lipophilic region, exhibited crystal- or plate-like structures, which formed a bilayer structure with a d spacing value of 3.93 nm. These results indicate that the self-assembly properties are strongly dependent on the type of double bond. Furthermore, 8 and 9, with the galactopyr anose moiety, revealed helical ribbon and well-defined double helical fiber structures, respectively. These findings support the view that the orientation of the intermolecular hydrogen-bonding interaction between the sugar moieties plays a critical role in producing the nanotubular structures. According to CD and powder XRD experiments, the relatively strong intermolecular hydrogen-bonding interaction of the glucopyranoside moiety in 3 and 4 provided a highly ordered chiral packing structure. Even though these compounds formed a weak hydrophobic interaction between lipophilic groups, it led to the formation of the nanotubular structure.

Sugar-derived gellant for hydrogel formation

A gelatinizer having gel-forming capability in both organic solvents and water, is provided. This invention is a hydrogelatinizer represented by: (where, A is a sugar residue, and R is an alkyl group).

Compositions and methods for targeted enzymatic release of cell regulatory compounds

Novel pro-drugs and methods for their use to alter the growth and biological characteristics of living cells, tissues, or whole organisms are described. The methods allow for selective activation of the pro-drugs at or near transformant host cells expressing a gene for an enzyme that activates the pro-drugs. Pro-drugs according to a preferred embodiment of the invention are conjugates of a bioactive compound and a chemical group that is capable of being cleaved from the bioactive compound by action of an enzyme. Methods according to this invention include, (a) introducing into targeted cells a gene encoding an enzyme and (b) administering a pro-drug, wherein the enzyme releases the pro-drug from conjugation. In a preferred embodiment of the invention, the gene encoding the enzyme is a marker gene.

Spectral characterization of self-assemblies of aldopyranoside amphiphilic gelators: What is the essential structural difference between simple amphiphiles and bolaamphiphiles?

An aldopyranoside-based gelators (dodecanoyl-p-aminophenyl-β-D-aldopyranoside)s and [1,12-dodecanedicarboxylic-bis(p-aminophenyl-β-D-aldopyranoside)]s 1-4 were synthesized, and their gelation ability was evaluated in organic solvents and water. Simple ald