BetaDxylopyranoside

Beta-D-xylopyranoside, commonly written beta-D-xylopyranoside, denotes any glycoside in which a β-D-xylopyranose unit is linked to an aglycone through the anomeric carbon. The designation specifies the β configuration at C1 and the xylose ring in its pyranose form. Because the aglycone can vary, beta-D-xylopyranosides form a broad class of compounds rather than a single molecule.

Structurally, the sugar moiety is the β-D-xylopyranose, a six-membered ring form of xylose. The glycosidic bond attaches at the anomeric carbon, and the nature of the aglycone determines the overall compound, influencing properties such as solubility and enzymatic recognition. The β configuration can affect hydrolysis rates and enzyme specificity compared with the α form.

Natural occurrence: β-D-xylopyranoside units appear in plant-derived glycosides and contribute to the composition of xylose-containing polysaccharides in plant cell walls, such as xylan backbones. In many cases, the xylose moiety serves as a linking unit within larger oligosaccharides or glycosides.

Applications: Beta-D-xylopyranoside derivatives are used in biochemistry and glycoscience as substrates and probes. A common example is p-nitrophenyl β-D-xylopyranoside, which serves as a colorimetric substrate for β-xylosidase activity assays, enabling measurement of enzyme kinetics and inhibitor screening.

Synthesis: Beta-D-xylopyranosides are typically prepared by glycosylation of an appropriate aglycone with protected β-D-xylosyl donors, followed by deprotection, or by epimerization strategies that establish the β linkage at the anomeric center.

See also: glycoside, xylopyranose, β-D-xylopyranoside substrates.