195385-93-4

Basic information

• Product Name: 4-Methylumbelliferylbeta-D-ribofuranoside
• Synonyms: 2H-1-Benzopyran-2-one, 4-methyl-7-(.beta.-D-ribofuranosyloxy)-;4-Methylumbelliferylb-D-ribofuranoside;4-Methylumbelliferyl β-D-ribofuranoside;4-Methyl-7-(beta-D-ribofuranosyloxy)-2H-1-benzopyran-2-one
• CAS NO: 195385-93-4
• Molecular Formula: C15H16O7
• Molecular Weight: 308.28300
• EINECS: 1533716-785-6
• Product Categories: substrate
• Mol File: 195385-93-4.mol

Chemical Properties

• Boiling Point: 599.4oC at 760 mmHg
• Flash Point: 228.1oC
• Appearance: /
• Density: 1.486g/cm3
• Vapor Pressure: 3.24E-15mmHg at 25°C
• Refractive Index: 1.631
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: 12.95±0.70(Predicted)
• CAS DataBase Reference: 4-Methylumbelliferylbeta-D-ribofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methylumbelliferylbeta-D-ribofuranoside(195385-93-4)
• EPA Substance Registry System: 4-Methylumbelliferylbeta-D-ribofuranoside(195385-93-4)

Safety Data

• Hazardous Substances Data: 195385-93-4(Hazardous Substances Data)

Usage

Uses

Used in Biochemical Research:
4-Methylumbelliferylbeta-D-ribofuranoside is used as a fluorogenic substrate for the detection and quantification of glycosidase enzyme activity. Its application is crucial in studying the kinetics and mechanisms of enzyme-catalyzed reactions.
Used in Enzyme Assays:
In the field of enzymology, 4-Methylumbelliferylbeta-D-ribofuranoside is used as a substrate to assay the activity of specific glycosidase enzymes, such as beta-D-glucosidases and beta-D-galactosidases, allowing for the assessment of their function and potential modulation by inhibitors or activators.
Used in Drug Screening:
4-Methylumbelliferylbeta-D-ribofuranoside is employed as a tool in drug screening processes to identify and characterize potential inhibitors or activators of glycosidase enzymes, which can be instrumental in the development of new therapeutic agents.
Used in Lysosomal Storage Disorder Research:
4-Methylumbelliferylbeta-D-ribofuranoside is used in the study of lysosomal storage disorders to investigate the consequences of glycosidase enzyme deficiencies, such as the accumulation of undigested substrates in the lysosomes of affected cells, providing insights into the pathophysiology of these conditions.

InChI:InChI=1/C15H16O7/c1-7-4-12(17)21-10-5-8(2-3-9(7)10)20-15-14(19)13(18)11(6-16)22-15/h2-5,11,13-16,18-19H,6H2,1H3/t11-,13-,14+,15-/m0/s1

Upstream product

• 106488-03-3 4-methylumbelliferyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranoside 
• 67909-28-8 β-7-hydroxy-4-methylcoumarin-7-yl D-galactofuranoside 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 84380-11-0 7-hydroxy-4-methyl-2-oxo-2H-1-benzopyran tetrabutylammonium salt 
• 172982-48-8 4-methylcoumarin-7-yl 2,3,4,6-tetra-O-benzoyl-β-D-galactofuranoside 
• 42868-96-2 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl bromide 

Relevant articles and documents

Based on 4 - methyl [...] synthesis method of a plurality of glycoside

The invention discloses a method for synthesizing various glucosides on a basis of 4-methylumbelliferone. According to the invention, a glycosyl donor peracetyl saccharide and a glycosyl acceptor 4-methylumbelliferone are subjected to a glycosylation reaction under room temperature or under heating with dichloromethane or 1,2-dichloroethane as a solvent and with the combined effect of Lewis acid boron trifluoride ethyl ether and organic alkali triethylamine or pyridine; and protecting groups are removed, such that various glucosides based on 4-methylumbelliferone can be obtained. The glucosides include 4-methylumbelliferone-beta-D-glucopyranosiduronide, 4-methylumbelliferone-beta-D-glucopyranoside, 4-methylumbelliferone-beta-D-xylopyranoside, 4-methylumbelliferone-beta-D-ribofuranoside, 4-methylumbelliferone-alpha-D-galactopyranoside, and 4-methylumbelliferone-alpha-D-mannopyranoside. The method is simple, and can produce a beta or alpha single-configuration target. A glycosylation reaction yield can reach 17-93%.

An improved helferich method for the α/β-stereoselective synthesis of 4-methylumbelliferyl glycosides for the detection of microorganisms

An improved Helferich method is presented. It involves the glycosylation of 4-methyl-umbelliferone with glycosyl acetates in the presence of boron trifluoride etherate combined with triethylamine, pyridine, or 4-dimethylaminopyridine under mild conditions, followed by deprotection to give fluorogenic 4-methylumbelliferyl glycoside substrates. Due to the use of base, the glycosylation reaction proceeds more easily, is uncommonly α- or β-stereoselective, and affords the corresponding products in moderate to excellent yields (51%-94%) under appropriate conditions.

ENZYME DETECTION/ASSAY METHOD AND SUBSTRATES

The invention relates to a method of detecting and/or assaying nucleoside hydrolases or nucleoside phosphorylases using a chromogenic substrate. Preferred chromogenic substrates have formula (I) where X is OH, or H, and Y is the residue of Y—OH where Y—OH is a chromophore or a compound readily converted to a chromophore and the substrates are hydrolysed by the nucleoside hydrolase to yield ribose or 2-deoxyribose plus Y—OH. Alternatively those substrates may be phosphorylysed by nucleoside phosphorylase to yield ribose-1-phosphate plus Y—OH. The methods may be used to detect and/or assay parasites in biological samples.

Synthesis of 4-methylcoumarin-7-yl β-D-galactofuranoside, a fluorogenic substrate for galactofuranosidase

Keywords: 4-Methylcoumarin-7-yl β-D-galactofuranoside; Fluorogenic substrate; Galactofuranosidase