128095-52-3

Usage

Uses

Used in Diagnostic Applications:
4-Methylumbelliferyl 2,3,4-tri-O-acetyl-α-L-idopyranosiduronic acid methyl ester is used as an intermediate in the synthesis of fluorogenic substrates for the fluorimetric enzyme assay. This assay is essential for the diagnosis of MPS II (Hunter disease), a rare genetic disorder characterized by the accumulation of complex molecules in the body due to the deficiency of α-L-iduronidase enzyme.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Methylumbelliferyl 2,3,4-tri-O-acetyl-α-L-idopyranosiduronic acid methyl ester is used as a key component in the development of diagnostic tools and therapies targeting MPS II (Hunter disease). Its role in the synthesis of fluorogenic substrates allows for the accurate detection and monitoring of the enzyme activity, which is crucial for the effective management of the disease.
Used in Research and Development:
4-Methylumbelliferyl 2,3,4-tri-O-acetyl-α-L-idopyranosiduronic acid methyl ester is also utilized in research and development for the study of α-L-iduronidase enzyme and its role in various biological processes. 4-Methylumbelliferyl2,3,4-tri-O-acetyl-a-L-idopyranosiduronicacidmethylester aids in understanding the molecular mechanisms underlying the development of MPS II and other related disorders, paving the way for the development of novel therapeutic strategies and interventions.

Upstream product

• 101014-65-7 methyl (4′-methylumbelliferyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)urinate 
• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 128095-50-1 4-methylcoumarin-7-yl-2,3,4-tri-O-acetyl-α-L-iduronic acid methyl ester 
• 56768-32-2 1-bromo-2,3,4-tri-O-acetyl-α-D-galactopyranuronic acid methyl ester 
• 5980-33-6 sodium 4-methylumbelliferonate 
• 929549-08-6 3,4,5-triacetoxy-6-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 67-56-1 methanol 
• 6160-80-1 4-methylumbelliferyl-β-D-glucuronide 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 

Relevant academic research and scientific papers

Practical Synthesis of the Fluorogenic Enzyme Substrate 4-Methylumbelliferyl α- L -Idopyranosiduronic Acid

A practical and concise synthesis of 4-methylumbelliferyl α- l -idopyranosiduronic acid, a fluorogenic enzyme substrate diagnostic for α- l -iduronidase, was accomplished. It features successive radical bromination and radical reduction of easily accessible methyl 4-methyl umbelliferyl-2,3,4-tri- O -acetyl-β- d -glucouronate in four steps with 28percent overall yield.

Synthetic method of fluorescent glycosidase substrate for determination of alpha-L-iduronidase

The invention relates to a synthesis method of a fluorescent glycosidase substrate for determination of alpha-L-iduronidase. According to the method, coumarin-beta-D-glucuronide is used as a raw material; the preparation method comprises the following steps: adding N-bromosuccinimide and a chlorinated organic solvent under an illumination condition by using a Wohl-Ziegler free radical reaction, and carrying out reflux stirring; then, spin-drying the organic solvent under reduced pressure; dissolving and extracting by using an organic solvent, collecting an organic phase, spin-drying the solvent, carrying out silica gel column chromatography separation to obtain a brominated compound, carrying out free radical reduction in the organic solvent, spin-drying the solvent, carrying out silica gel column chromatography separation to obtain coumarin-alpha-L-iduronide, and finally removing a protecting group to obtain coumarin-alpha-L-iduronide. The coumarin-alpha-L-iduronide is synthesized bya method of free radical substitution and reduction of coumarin-beta-D-glucuronide for the first time, and the reaction has the characteristics of simplicity and convenience in operation, simple and easily available raw materials, easiness in product separation, high reaction yield and the like.

AN ESTERIFICATION/SAPONIFICATION-BASED METHOD FOR LIPOSOMAL LOADING

Described herein is a method for loading a hydrophilic compound into liposomes after addition of an alkylester group to form an esterified compound. After loading, the alkylester is hydrolyzed to reform the hydrophilic compound inside the liposomes. Also described is a method for loading drugs under a glucuronide methylester form into liposomes. The glucuronide methylester form of the drug is saponified to a glucuronide form of the drug inside the liposomes for better drug retention. The glucuronide residue conjugated to drugs can be removed inside cells to regenerate the parental drug upon cell uptake, liposomal degradation and enzyme hydrolysis. In case of cancer, this method can be used to safely deliver drugs to tumors.

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.