18997-57-4

Basic information

• Product Name: 4-Methylumbelliferyl-beta-D-glucopyranoside
• Synonyms: 4-methylumbelliferylglucoside;7-(beta-d-glucopyranosyloxy)-4-methyl-2h-1-benzopyran-2-on;MUD;MUGGAL;MUGLUCOSIDE;MUG;MU-GAL;MUGALACTOSIDE
• CAS NO: 18997-57-4
• Molecular Formula: C₁₆H₁₈O₈
• Molecular Weight: 338.31
• EINECS: 228-185-5
• Product Categories: Substrates;Carbohydrates & Derivatives;Fluorescent Labels & Indicators;substrate
• Mol File: 18997-57-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 258-263 °C (dec.)
• Boiling Point: 394.46°C (rough estimate)
• Flash Point: 233.9 °C
• Appearance: White to off-white/Powder
• Density: 1.522
• Refractive Index: 1.4430 (estimate)
• Storage Temp.: 2-8°C
• PKA: 12.73±0.70(Predicted)
• Water Solubility: Soluble in DMF or water
• BRN: 94672
• CAS DataBase Reference: 4-Methylumbelliferyl-beta-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methylumbelliferyl-beta-D-glucopyranoside(18997-57-4)
• EPA Substance Registry System: 4-Methylumbelliferyl-beta-D-glucopyranoside(18997-57-4)

Safety Data

• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 18997-57-4(Hazardous Substances Data)

Usage

Description

4-Methylumbelliferyl-β-D-Glucopyranoside (4-MUG) is a fluorogenic substrate of β-glucosidase and β-glucocerebrosidase (also known as glucosylceramidase). In addition to its use in characterizing novel β-glucosidases, 4-MUG is used in assays to evaluate deficiency in β- glucocerebrosidase activity related to Gaucher disease. Hydrolysis of 4-MUG releases the fluorescent product 4-MU, which has an emission maximum at 445-454 nm. The excitation maximum for 4-MU is pH-dependent: 330, 370, and 385 nm at pH 4.6, 7.4, and 10.4, respectively.

Chemical Properties

White Powder

Uses

Different sources of media describe the Uses of 18997-57-4 differently. You can refer to the following data:
1. A fluorogenic substrate in the assay of ?-glucosidase. Fluorescence: max. Abs. 316nm; max. Em. 372nm; e x 10-3: 15
2. A fluorogenic substrate in the assay of ?-glucosidase.Fluorescence: max. Abs. 316nm; max. Em. 372nm; e x 10-3: 15
3. 4-Methylumbelliferyl β-D-glucopyranoside has been used as substrate:in glucosylceramidase β enzyme activity assay in lysosome-enriched fractions from primary hippocampal neuronsin β-glucosidase assay during yeast fermentationto assay glucocerebrosidase 1 (GBA1)-related glucosidase activity in macrophage cell line (RAW)

Definition

ChEBI: A beta-D-glucoside having a 4-methylumbelliferyl substituent at the anomeric position.

Biochem/physiol Actions

4-Methylumbelliferyl β-D-glucopyranoside is a synthetic enzymatic substrate for glycosidase. It has been used as substrate for the β- glucosidase from enterococci.

Purification Methods

4-Methylumbellifer-7-yl--Dglucopyranoside crystallises as the half hydrate from hot H2O. [Constantzas & Kocourek Collect Czech Chem Commun 24 1099 1959, De Re et al. Ann Chim (Rome) 4 9 2089 1959, Courtin-Duchateau & Veyrière Carbohydr Research 65 23, 29 1978, Beilstein 18 III/IV 5152, 8 IV 433, 18/7 V 616.]

Upstream product

• 67909-25-5 4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 618879-31-5 4-methylumbelliferyl β-laminaratetraoside 
• 618879-32-6 4-methylumbelliferyl β-laminarapentaoside 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-68-2 α-D-glucopyranose peracetylate 
• 133-89-1 UDP-glucose 
• 83-87-4 D-glucose pentaacetate 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 74808-10-9 2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate 
• 63700-19-6 uridine-5'-diphospho-α-D-glucuronic acid trisodium salt 
• 604-69-3 β-D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 4336-91-8 3-bromo-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 

Downstream Products

• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 50-99-7 D-glucose 
• 2280-44-6 D-Glucose 
• 72626-61-0 4-methylumbellifer-7-yl-β-D-cellobioside 
• 172364-08-8 4-methylumbelliferyl 3-O-β-D-glucopyranosyl-β-D-glucopyranoside 
• 172364-16-8 4-methylumbelliferyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 172364-23-7 7-[(2S,3R,4S,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4-methyl-chromen-2-one 
• 172364-19-1 4-methylumbelliferyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1<*>3)-2-O-benzyl-4,6-benzylidene-β-D-glucopyranoside 
• 172364-20-4 4-methylumbelliferyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1<*>4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1<*>3)-2-O-benzyl-4,6-benzylidene-β-D-glucopyranoside 
• 73448-32-5 4-methylumbelliferyl β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside 
• 937018-35-4 4-methylumbelliferyl-2,3,4-tri-O-acetyl-6-O-trityl-β-D-glucopyranoside 
• 492-61-5 β-D-glucose 
• 172364-12-4 4-methylumbelliferyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 6160-80-1 4-methylumbelliferyl-β-D-glucuronide 

Relevant articles and documents

OleD Loki as a Catalyst for Tertiary Amine and Hydroxamate Glycosylation

We describe the ability of an engineered glycosyltransferase (OleD Loki) to catalyze the N-glycosylation of tertiary-amine-containing drugs and trichostatin hydroxamate glycosyl ester formation. As such, this study highlights the first bacterial model catalyst for tertiary-amine N-glycosylation and further expands the substrate scope and synthetic potential of engineered OleDs. In addition, this work could open the door to the discovery of similar capabilities among other permissive bacterial glycosyltransferases.

The Novel UDP Glycosyltransferase 3A2: Cloning, catalytic properties, and tissue distribution

The human UDP glycosyltransferase (UGT) 3A family is one of three families involved in the metabolism of small lipophilic compounds. Members of these families catalyze the addition of sugar residues to chemicals, which enhances their excretion from the body. The UGT1 and UGT2 family members primarily use UDP glucuronic acid to glucuronidate numerous compounds, such as steroids, bile acids, and therapeutic drugs. We showed recently that UGT3A1, the first member of the UGT3 family to be characterized, is unusual in using UDP N-acetylglucosamine as sugar donor, rather than UDP glucuronic acid or other UDP sugar nucleotides (J Biol Chem 283:36205-36210, 2008). Here, we report the cloning, expression, and characterization of UGT3A2, the second member of the UGT3 family. Like UGT3A1, UGT3A2 is inactive with UDP glucuronic acid as sugar donor. However, in contrast to UGT3A1, UGT3A2 uses both UDP glucose and UDP xylose but not UDP N-acetylglucosamine to glycosidate a broad range of substrates including 4-methylumbelliferone, 1-hydroxypyrene, bioflavones, and estrogens. It has low activity toward bile acids and androgens. UGT3A2 transcripts are found in the thymus, testis, and kidney but are barely detectable in the liver and gastrointestinal tract. The low expression of UGT3A2 in the latter, which are the main organs of drug metabolism, suggests that UGT3A2 has a more selective role in protecting the organs in which it is expressed against toxic insult rather than a more generalized role in drug metabolism. The broad substrate and novel UDP sugar specificity of UGT3A2 would be advantageous for such a function. Copyright

Solvent-Dependent Mechanism and Stereochemistry of Mitsunobu Glycosylation with Unprotected Pyranoses

An SN2 mechanism was proposed for highly stereoselective glycosylation of benzoic acid with unprotected α-d-glucose under Mitsunobu conditions in dioxane, while an SN1 mechanism was indicated for nonstereoselective glycosylation in DMF. The SN2-type stereoselective Mitsunobu glycosylation is generally applicable to various unprotected pyranoses as glycosyl donors in combination with a wide range of acidic glycosyl acceptors such as carboxylic acids, phenols, and imides, retaining its high stereoselectivity (33 examples). Glycosylation of a carboxylic acid with unprotected α-d-mannose proceeded also in an SN2 manner to directly afford a usually less accessible 1,2-cis-mannoside. One-or two-step total syntheses of five simple natural glycosides were performed using the glycosylation strategy presented here using unprotected α-d-glucose.

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%.