Toward the solid-phase synthesis of heparan sulfate oligosaccharides: evaluation of iduronic acid and idose building blocks.

Glycan arrays have been established as the premier technical platform for assessing the specificity of carbohydrate binding proteins, an important step in functional glycomics research. Access to large libraries of well-characterized oligosaccharides remains a major bottleneck of glycan array research, and this is particularly true for glycosaminoglycans (GAGs), a class of linear sulfated polysaccharides which are present on most animal cells. Solid-supported synthesis is a potentially powerful tool for the accelerated synthesis of relevant GAG libraries with variations in glycan sequence and sulfation pattern.

A new linker for solid-phase synthesis of heparan sulfate precursors by sequential assembly of monosaccharide building blocks.

A novel ester type linker which upon cleavage releases the glycans as carbamate protected aminoglycosides was successfully employed in the sequential assembly of L-idose and azido glucose monosaccharide building blocks to heparan sulfate precursors.

Hydration index--a better parameter for explaining small molecule hydration in inhibition of ice recrystallization.

Several simple mono- and disaccharides have been assessed for their ability to inhibit ice recrystallization. Two carbohydrates were found to be effective recrystallization inhibitors. D-galactose (1) was the best monosaccharide and D-melibiose (5) was the most active disaccharide.