296776-03-9

Usage

Uses

Used in Chemical Research:
4-Methylumbelliferyl 6-O-(tert-Butyldiphenylsilyl)-β-D-galactopyranoside is used as an intermediate in the production of fluorescent indicators. Its unique structure allows for the development of sensitive and selective assays, which are crucial for monitoring various biochemical processes.
Used in Enzyme Assays:
In the field of biochemistry, 4-Methylumbelliferyl 6-O-(tert-Butyldiphenylsilyl)-β-D-galactopyranoside serves as a substrate for determining sulphatase activity. Sulphatases are a class of enzymes that catalyze the removal of sulfate groups from various substrates. By using 4-Methylumbelliferyl 6-O-(tert-Butyldiphenylsilyl)-β-D-galactopyranoside as a substrate, researchers can accurately measure the activity of sulphatases, which is essential for understanding their role in biological systems and diagnosing related diseases.
Used in Pharmaceutical Development:
Due to its ability to act as a substrate for sulphatases, 4-Methylumbelliferyl 6-O-(tert-Butyldiphenylsilyl)-β-D-galactopyranoside can be employed in the development of drugs targeting these enzymes. This may lead to the discovery of novel therapeutic agents for the treatment of diseases associated with altered sulphatase activity.
Used in Analytical Chemistry:
The fluorescent properties of 4-Methylumbelliferyl 6-O-(tert-Butyldiphenylsilyl)-β-D-galactopyranoside make it a valuable tool in analytical chemistry. It can be used to develop sensitive detection methods for various compounds, including sulphatases and their substrates, by employing fluorescence-based techniques such as high-performance liquid chromatography (HPLC) or fluorescence spectroscopy.

Upstream product

• 281207-18-9 2-(2',3',4',6'-tetra-O-acetyl-α-D-galactopyranosyloxy)-1,3,2-dioxaphosphinane 2-oxide 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 6160-79-8 4-methylumbelliferyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 6160-78-7 4-methylumbelliferyl-β-D-galactopyranoside 

Downstream Products

• 920975-58-2 4-methylumbelliferyl-2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside 
• 920975-61-7 4-methylumbelliferyl[methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate]-(2->3)-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside 
• 296776-06-2 4-methylumbelliferyl 3-O-(α-L-fucopyranosyl)-β-D-galactopyranoside 
• 296776-04-0 4-methylumbelliferyl 6'-O-(tert-butyldiphenylsilyl)-3'-O-(2'',3'',4''-tri-O-acetyl-α-L-fucopyranosyl)-β-D-galactopyranoside 

Relevant academic research and scientific papers

Natural sialoside analogues for the determination of enzymatic rate constants

Two isomeric 4-methylumbelliferyl-α-d-N- acetylneuraminylgalactopyranosides (1 and 2) were synthesised. These compounds contain either the natural α-2,3 or α-2,6 sialyl-galactosyl linkages, as well as an attached 4-methylumbelliferone for convenient detection of their hydrolyses. These compounds were designed as natural sialoside analogues to be used in a continuous assay of sialidase activity, where the sialidase-catalysed reaction is coupled with an exo-β-galactosidase- catalysed hydrolysis of the released galactoside to give free 4-methylumbelliferone. The kinetic parameters for 1 and 2 were measured using the wild-type and nucleophilic mutant Y370G recombinant sialidase from Micromonospora viridifaciens. Kinetic parameters for these analogues measured using the new continuous assay were in good agreement with the parameters for the natural substrate, 3′-sialyl lactose. Given the selection of commercially available exo-β-galactosidases that possess a variety of pH optima, this new method was used to characterise the full pH profile of the wild-type sialidase with the natural sialoside analogue 1. Thus, use of these new substrates 1 and 2 in a continuous assay mode, which can be detected by UV/Vis or fluorescence spectroscopy, makes characterisation of sialidase activity with natural sialoside linkages much more facile. The Royal Society of Chemistry.

Stereoselective synthesis of α-L-Fucp-(1,2)- and -(1,3)-β-D-Galp(1)-4-methylumbelliferone using glycosyl donor substituted by propane-1,3-diyl phosphate as leaving group

Stereoselective synthesis of α-L-Fucp-(1,2)- and -(1,3)-β-D-Galp(1)-4-methyllumbelliferone was accomplished using glycosyl donor substituted by propane-1,3-diyl phosphate as leaving group. The α-stereochemistry for the anomeric centre was assigned on the basis of the observed 13C-H coupling constant of 165.4 Hz for the bond. The results suggested that the bond-forming reaction intermediate was formed through participation of the second carbon acetoxy function or by an SN2-like process.