66901-41-5

Usage

Uses

Used in Biochemical Assays:
4-Methylumbelliferyla-L-idopyranoside is used as a fluorogenic substrate for the detection and measurement of α-L-iduronidase enzyme activity. This application is particularly important in the field of molecular biology and biochemistry, as it aids in the study of enzyme kinetics and the understanding of enzyme function.
Used in Medical Diagnostics:
In the medical diagnostics industry, 4-Methylumbelliferyla-L-idopyranoside is used as a diagnostic tool for the detection of Hurler's syndrome, also known as mucopolysaccharidosis type I (MPS I). This is a rare genetic disorder characterized by the accumulation of mucopolysaccharides in the body, leading to various health complications. The use of 4-MUI in diagnostic assays helps in the early identification and management of this condition.
Used in Research and Development:
4-Methylumbelliferyla-L-idopyranoside is also utilized in research and development for the study of enzyme mechanisms, enzyme inhibition, and the development of new therapeutic strategies targeting α-L-iduronidase. Its role in these applications contributes to the advancement of scientific knowledge and the potential development of novel treatments for related diseases.

Upstream product

• 66895-31-6 1-(4-methylumbelliferone)-2,3,4,6-tetra-O-acetyl-α-L-idopyranose 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 330974-67-9 1,2,3,4,6-penta-O-acetyl-L-idopyranose 
• 14795-18-7 Acetic acid (2S,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-bromo-tetrahydro-pyran-4-yl ester 
• 2152-77-4 1,2,3,4,6-penta-O-acetyl-α-L-idopyranose 

Downstream Products

• 66966-09-4 4-methylcoumarin-7-yl α-L-idopyranosiduronic acid 
• 76-84-6 triphenylmethyl alcohol 
• 89157-95-9 4-methylcoumarin-7-yl 2,3,4-O-acetyl-6-O-triphenylmethyl-α-L-idopyranose 
• 84434-84-4 4-methylcoumarin-7-yl-α-L-iduronic acid 

Relevant academic research and scientific papers

Method for the diagnosis of lysosomal storage diseases

The present invention relates to a method for the diagnosis of a lysosomal storage disease (LSD) in a subject which is based on determining the activity of lysosomal enzymes with the help of 4-alkyl umbelliferyl derivatives. The present invention further relates to said 4-alkyl umbelliferyl derivatives for use in the diagnosis of an LSD, and a kit for the diagnosis of an LSD.

From D-Glucose to Biologically Potent L-Hexose Derivatives: Synthesis of α-L-Iduronidase Fluorogenic Detector and the Disaccharide Moieties of Bleomycin A2 and Heparan Sulfate

A novel and convenient route for the synthesis of biologically potent and rare L-hexose derivatives from D-glucose is described. Conversion of diacetone-α-D-glucose (14) into 1,2:3,5-di-O-isopropylidene-β -L-idofuranose (19) was efficiently carried out in two steps. Orthogonal isopropylidene rearrangement of compound 19 led to 1,2:5,6-di-O-isopropylidene-β-L-idofuranose (27), which underwent regioselective epimerization at the C3 position to give the L-talo- and 3-functionalized L-idofuranosyl derivatives. Hydrolysis of compound 19 under acidic conditions furnished 1,6-anhydro-β-L-idopyranose (35) in excellent yield, which was successfully transformed into the corresponding L-allo, L-altro, L-gulo, and L-ido derivatives via regioselective benzylation, benzoylation, triflation and nucleophilic substitution as the key steps. Applications of these 1,6-anhydro-β-L-hexopyranoses as valuable building blocks to the syntheses of 4-methylcoumarin-7-yl-α-L-iduronic acid and the disaccharide moieties of bleomycin A2 as well as heparan sulfate are highlighted.

SYNTHESIS OF SOME ARYL 2,3,4,6-TETRA-O-ACETYL-L-IDOPYRANOSIDES AND OF 4-METHYLCOUMARIN-7-YL α-L-IDOPYRANOSIDURONIC ACID

Several routes for synthesis of 3,5,6-tri-O-acetyl-1,2-O-isopropylidene-β-L-idofuranose have been evaluated.Previously described routes, which involved selective sulphonylation, were not reproducible on a 100-g scale.To overcome this difficulty, a new variation was developed, involving complete tosylation of 1,2-O-isopropylidene-α-D-glucofuranurono-6,3-lactone followed by reduction and acetylation.The idofuranose derivative was converted into the desired 1,2,3,4,6-penta-O-acetyl-α-L-idopyranose via 1,6-anhydro-β-L-idopyranose.Fusion of 1,2,3,4,6-penta-O-acetyl-α-L-idopyranose with 4-nitrophenol, 1- or 2-naphtol, or 4-methylcoumarin-7-ol, using freshly fused zinc chloride as catalyst, gave an anomeric mixture of glycosides, with the α anomer being preponderant.The major 4-methylcoumarin-7-yl glycoside was deacylated and converted, by catalytic oxidation, into 4-methylcoumarin-7-yl α-L-idopyranosiduronic acid, fluorogenic substrate for α-L-iduronidase.