69414-26-2

Usage

Uses

4-Methylumbelliferyl alpha-L-arabinopyranoside is a derivative of arabinopyranose.

Definition

ChEBI: An alpha-L-arabinopyranoside having a 4-methylumbelliferyl substituent at the anomeric position

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

Upstream product

• 6734-34-5 4′-methylumbelliferyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 2001-96-9 p-nitrophenyl β-D-xylopyranoside 
• 3616-06-6 UDP-xylose 
• 3945-26-4 α-D-xylopyranosyl fluoride 
• 4627-30-9 (3R,4R,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 
• 10369-25-2 (3R,4R,5R)-2-hydroxytetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 869848-87-3 C₁₃H₁₆Cl₃NO₈ 
• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 197144-02-8 2,3,4-tri-O-acetyl-D-xylopyranosyl trichloroacetimidate 
• 106820-14-8 2,3,4-Tri-O-acetyl-D-xylopyranose 
• 62446-93-9 1,2,3,4-tetra-O-acetyl-D-xylopyranose 
• 3068-31-3 1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose 

Downstream Products

• 158962-91-5 4-methylumbelliferyl β-D-xylopyranosyl-(1->4)-β-D-xylopyranoside 

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.

α-Thioglycoligase-based synthesis of O-aryl α-glycosides as chromogenic substrates for α-glycosidases

α-Thioglycoligases are retaining α-glycosidase mutants, with modification of their general acid/base catalytic residue to an inactive amino acid residue, catalyzing the formation of S-glycosidic linkages using a sugar donor with an excellent leaving group and suitable sugar acceptors with a thiol group as the substrate. In this study, we describe the enzymatic synthesis of O-aryl α-glycosides catalyzed by α-thioglycoligases. An α-xylosidase mutant (YicI-D482A) efficiently catalyzed the synthesis of O-aryl α-xylosides in near-quantitative yields (up to 99%) using 4-methylumbelliferone and nitrophenols. Synthesis did not occur with those acceptors having a nitro group at the ortho-position. The conversion yields of 3-nitrophenol markedly increased at pH 8.0, whereas those of other aryl compounds were nearly independent of pH, ranging from pH 6.0 to 8.0. The O-aryl α-xylosides were prepared on a preparative scale with yields of up to 96%. Upon employing the O-aryl α-xylosides as the substrate for the wild-type YicI, Br?nsted relationships of log kcat versus pKa and log (kcat/KM) versus pKa both showed a linear monotonic dependence on the leaving group pKa with low βlg values of 0.39 and 0.38, respectively. In addition, synthesis of O-aryl α-glucosides was successfully conducted by an α-glucosidase mutant (MalA-D416A) in the same fashion with high yields. Therefore, this strategy can be used for the synthesis of O-aryl α-glycosides using an acid/base mutant of retaining α-glycosidases that hydrolyze the glycosides.

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.

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

β-D-GLUCOSIDASE-CATALYSED TRANSFER OF THE GLYCOSYL GROUP FROM ARYL β-D-GLUCO- AND β-D-XYLO-PYRANOSIDES TO PHENOLS

The effect of phenols on the hydrolysis of substituted phenyl β-D-gluco- and β-D-xylo-pyranosides by β-D-glucosidase from Stachybotrys atra has been investigated.Depending on the glycon part of the substrate and on the phenol substituent, the hydrolysis is either inhibited or activated.With aryl β-D-glucopyranosides, such transfer does not occur when phenols are used as acceptors, but it does occur with anilines.A two-steps mechanism, in which the first step is partially reversible, is proposed to explain these observations.A qualitative analysis of the various factors determing the overall effect of the phenol is given.