17306-99-9

Usage

InChI:InChI=1/C15H16O5/c16-11-8-19-15(14(18)13(11)17)20-12-7-3-5-9-4-1-2-6-10(9)12/h1-7,11,13-18H,8H2/t11-,13+,14-,15+/m1/s1

Upstream product

• 17306-80-8 1-naphthyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside 
• 90-15-3 α-naphthol 
• 3068-31-3 1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose 
• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 

Relevant academic research and scientific papers

Exploration of the active site of β4GalT7: Modifications of the aglycon of aromatic xylosides

Proteoglycans (PGs) are macromolecules that consist of long linear polysaccharides, glycosaminoglycan (GAG) chains, covalently attached to a core protein by the carbohydrate xylose. The biosynthesis of GAG chains is initiated by xylosylation of the core protein followed by galactosylation by the galactosyltransferase β4GalT7. Some β-d-xylosides, such as 2-naphthyl β-d-xylopyranoside, can induce GAG synthesis by serving as acceptor substrates for β4GalT7 and by that also compete with the GAG synthesis on core proteins. Here we present structure-activity relationships for β4GalT7 and xylosides with modifications of the aromatic aglycon, using enzymatic assays, cell studies, and molecular docking simulations. The results show that the aglycons reside on the outside of the active site of the enzyme and that quite bulky aglycons are accepted. By separating the aromatic aglycon from the xylose moiety by linkers, a trend towards increased galactosylation with increased linker length is observed. The galactosylation is influenced by the identity and position of substituents in the aromatic framework, and generally, only xylosides with β-glycosidic linkages function as good substrates for β4GalT7. We also show that the galactosylation ability of a xyloside is increased by replacing the anomeric oxygen with sulfur, but decreased by replacing it with carbon. Finally, we propose that reaction kinetics of galactosylation by β4GalT7 is dependent on subtle differences in orientation of the xylose moiety. This journal is

Synthesis of 2- and 4-nitrophenyl β-glycosides of β-(1 → 4)-D-xylo-oligosaccharides of dp 2-4

2- and 4-Nitrophenyl β-D-xylopyranosides (4 and 5) were transformed, via dibutyltin oxide-mediated acylation, into the corresponding 2,3-di-O-benzoyl derivatives 11 and 15. Xylobiose and xylotriose were easily isolated by charcoal column chromatography from a commercially available material and converted into the di- and trisaccharide methyl 1-thio-β-glycosides 36 and 37. The 2- and 4-nitrophenyl β-glycosides of the β-(1 → 4)-D-xylo-oligosaccharides of dp 2-4 were synthesized by N-iodosuccinimide-silver triflate-promoted condensation using 11 and 15 as the glycosyl acceptors and ethyl 1-thio-β-D-xylopyranoside triacetate 16, 36, and 37 as the glycosyl donors. Also described are an improved preparation of 4 and 5, and the synthesis of 1-naphthyl β-D-xylopyranoside, as well as an alternative approach to the 2- and 4-nitrophenyl β-xylobiosides.