5041-91-8

Upstream product

• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 108-95-2 phenol 
• 1141-01-1 (3R,4S,5R)-2-Phenoxy-tetrahydro-pyran-3,4,5-triol 
• 108-24-7 acetic anhydride 
• 108-98-5 thiophenol 
• 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 
• 87-72-9 D-Xylose 
• 17296-18-3 2,3,4-tri-O-chlorosulfonyl-β-D-xylopyranosyl chloride 
• 3068-31-3 2,3,4-tri-O-acetyl-α-D-xylopyranosyl bromide 

Downstream Products

• 4756-31-4 phenyl β-D-xylopyranoside 
• 144683-64-7 (2S,3R,4S,5R,6R)-2-((3R,4R,5R,6S)-4,5-Dihydroxy-6-phenoxy-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 144683-63-6 (2S,3R,4S,5R,6R)-2-((2S,3R,4S,5R)-3,5-Dihydroxy-2-phenoxy-tetrahydro-pyran-4-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 20452-28-2 phenyl 1-thio-β-D-xylopyranoside 

Relevant academic research and scientific papers

The application of aryl substituted derivatives of xylose as environmentally friendly multipurpose pesticides

A series of aryl substituted derivatives of xylose have been synthesized. Biological tests have revealed high fungicidal activity of the resulting compounds against various phythopathogenic fungi. Additional biological studies have demonstrated high plant growth regulatory activity of the compounds synthesized.

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 phalluside-1 and Sch II using 1,2-metallate rearrangements

(4E,8E,10E)-9-Methyl-4,8,10-sphingatrienine, a core component of marine sphingolipids, was synthesised for the first time using a copper(i)-mediated 1,2-metallate rearrangement of a lithiated glycal as a key step. It was converted to phalluside-1, a cereb

Synthesis and evaluation of potential inhibitors of chondroitin AC lyase from Flavobacterium heparinum

Chondroitin AC lyase from Flavobacterium heparinum degrades chondroitin sulfate glycosaminoglycans via an elimination mechanism, resulting in disaccharides or oligosaccharides with Δ4,5-unsaturated uronic acid residues at their nonreducing end. The syntheses and testing of two potential inhibitors of this lyase are described. Methyl O-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1→4)-α -L-threo-hex-4-enopyranoside, 1, has the trigonal geometry at C5 of the uronic acid moiety expected at the transition state, yet retains the "leaving group" sugar moiety. Surprisingly, compound 1 showed no inhibition of the enzyme. The novel 5-nitro sugar, phenyl (5S)-5-nitro-β- D-xylopyranoside, 2, is a monosaccharide nitro analogue of the natural substrate, with C5 being a carbon acid of pKa 8.8. The rate of reprotonation of the anion generated at this center is sufficiently low that the anion of 2 can be used directly in initial steady-state velocity measurements without significant interference from the conjugate carbon acid. The anion of compound 2 was found to be a competitive inhibitor with a Ki value of 5 mM, whereas the conjugate acid had a Ki value of 35 mM.

Enzymatic β-galactosidation of modified monosaccharides: Study of the enzyme selectivity for the acceptor and its application to the synthesis of disaccharides

The selectivity of the E. coli β-galactosidase-catalyzed glycosylation of monosaccharides differently substituted at the anomeric position has been studied. Substituents bearing a phenyl ring increase the enzyme-acceptor binding; however, partial enzyme inhibition occurs. The regioselectivity of the glycosylation was dependent on small variations in the monosaccharide acceptor, such as the atom linked to the anomeric carbon and the number of methylenes between this atom and aromatic ring. A schematic model is proposed that accounts for the results. The information from this study allows the direct synthesis of disaccharides, with high regioselectivity and yields ranging from 30 to 40%.

Benzylphenyl osides, method of preparation and use therefor

The present invention relates, by way of new industrial products, to the benzylphenyl osides of the formula STR1 in which: X1, X2, X3, X4 and X5, which are identical or different, each represent a hyd