28541-83-5

Usage

Uses

Used in Enzyme Assays:
4-METHYLUMBELLIFERYL BETA-D-MANNOPYRANOSIDE is used as a substrate for mannosidase and N-acetyl-α-D-glucosaminidase enzymes. It is particularly useful in enzyme assays, where it helps in the detection and quantification of these enzymes' activities. The hydrolysis of 4-MU-beta-D-Mannopyranoside by these enzymes releases 4-methylumbelliferone, a fluorescent compound that can be easily measured, allowing for the assessment of enzyme activity.
Used in Analytical Chemistry:
4-METHYLUMBELLIFERYL BETA-D-MANNOPYRANOSIDE is used as an analytical reagent for studying biomass degradation by fungi. Its ability to act as a substrate for mannosidase enzymes makes it a valuable tool in understanding the enzymatic processes involved in the breakdown of complex carbohydrates in biomass, which has significant implications for biofuel production and other industrial applications.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-METHYLUMBELLIFERYL BETA-D-MANNOPYRANOSIDE is used as a research tool to study the inhibition and activity of glycosidase enzymes, which are often targeted in the development of drugs for various diseases, including lysosomal storage disorders and cancer. Its role in enzyme assays aids in the identification and optimization of potential drug candidates.
Used in Biotechnology:
In the biotechnology sector, 4-METHYLUMBELLIFERYL BETA-D-MANNOPYRANOSIDE is employed as a substrate for the study of enzyme kinetics, enzyme inhibition, and enzyme mechanism. Its use in these studies contributes to the development of biotechnological applications, such as the production of biofuels, bioplastics, and other bio-based materials derived from biomass.

Upstream product

• 28541-71-1 4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 83-87-4 D-Mannose pentaacetate 
• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 
• 5980-33-6 sodium 4-methylumbelliferonate 

Relevant academic research and scientific papers

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.

CARBONIC ANHYDRASE INHIBITORS WITH ANTIMETASTATIC ACTIVITY

Compositions for the treatment of cancer comprising coumarin and thiocoumarin derivatives of Formulas I- XII are disclosed. Said derivatives preferentially inhibit carbonic anhydrase IX and XII (which are associated with hypoxic and metastatic tumours) over inhibiting carbonic anhydrase I and II activity. The compositions therefore are suited for treatment of hypoxic or metastatic cancers due to this selective mechanism of action.

Glycosyl coumarin carbonic anhydrase IX and XII inhibitors strongly attenuate the growth of primary breast tumors

A series of 7-substituted coumarins incorporating various glycosyl moieties were synthesized and investigated for the inhibition of the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1). These coumarins were very weak or ineffective as inhibitors of the housekeeping, offtarget isoforms CA I and II, but some of them inhibited tumor-associated CA IX and XII in the low nanomolar range. They also significantly inhibited the growth of primary tumors by the highly aggressive 4T1 syngeneic mouse mammary tumor cells at 30 mg/kg, constituting interesting candidates for the development of conceptually novel anticancer drugs. Because CA IX is overexpressed in hypoxic tumors and exhibits very limited expression in normal tissues, such compounds may be useful for treating cancers not responsive to classic chemo- and radiotherapy.

COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS

The present invention encompasses compounds and methods for treating urinary tract infections.

Profiling of glycosidase activities using coumarin-conjugated glycoside cocktails

Glycosidases are a large subgroup of carbohydrate-processing enzymes that hydrolytically cleave the glycosidic bond. Glycans formed by the action of glycosidases are involved in various biological processes. Genetic abnormalities in glycosidases are associated with inherited diseases. Thus, characterization of the catalytic activities of glycosidases is of great importance. Herein, we describe a simple and rapid approach for determining glycosidase activity profiles using coumarin-conjugated glycoside cocktails.