65502-34-3

Basic information

• Product Name: 2H-1-Benzopyran-2-one, 4-methyl-7-(beta-D-xylosyloxy)-
• Synonyms: 2H-1-Benzopyran-2-one, 4-methyl-7-(beta-D-xylosyloxy)-
• CAS NO: 65502-34-3
• Molecular Weight: 0
• Mol File: 65502-34-3.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2H-1-Benzopyran-2-one, 4-methyl-7-(beta-D-xylosyloxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1-Benzopyran-2-one, 4-methyl-7-(beta-D-xylosyloxy)-(65502-34-3)
• EPA Substance Registry System: 2H-1-Benzopyran-2-one, 4-methyl-7-(beta-D-xylosyloxy)-(65502-34-3)

Safety Data

• Hazardous Substances Data: 65502-34-3(Hazardous Substances Data)

Upstream product

• 6734-34-5 4′-methylumbelliferyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside 
• 3616-06-6 UDP-xylose 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 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 
• 2001-96-9 p-nitrophenyl β-D-xylopyranoside 

Downstream Products

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

Relevant articles and documents

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%.

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.

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.