Synthesis of Carbohydrate Building Blocks for Automated Oligosaccharide Construction

Recent Developments in Solid-Phase Glycan Synthesis

“…57 Some BBs are now commercially available and approaches to automate their synthesis are emerging. 58 However, the preparation of properly protected BBs can be time-consuming, often requiring several synthetic transfor-mations. Recently, a biocatalytic approach assisted the preparation of a selectively protected N-acetyllactosamine (LacNAc) motif, which, after a few chemical manipulations, was employed in the solid-phase synthesis of a tetrasaccharide.…”

Development of Recyclable Polystyrene-Supported Phosphonic Acid Resins for Carbohydrate Immobilization and Glycosylation

“…Since the work by Frechet and Schuerch in the early 1970s, solid-phase synthesis has been of great importance to carbohydrate chemistry . As demonstrated by the pioneering studies of Seeberger and co-workers, and, others, automated solid-phase synthesis has transformed the assembly of complex oligosaccharides and greatly impacted various fields of chemistry, biology, and material science . The developments in the aforementioned areas would not be possible without the emergence of new methods for loading and cleaving the glycosyl moiety to/from the resin during the various stages of solid-phase carbohydrate synthesis.…”

“…The developments in the aforementioned areas would not be possible without the emergence of new methods for loading and cleaving the glycosyl moiety to/from the resin during the various stages of solid-phase carbohydrate synthesis. The position of carbohydrate attachment may happen at both the anomeric position or other hydroxyl groups, and a variety of linkers at the anomeric position, including thioglycosides, photocleavable benzyl glycosides, allylic alcohol glycosides, and esters have been developed. , These methods are tailored to the on-resin oligosaccharide assembly and do not directly involve the use of the acetal end of the linked oligosaccharide for glycosylation reactions (cf. Figure A,B).…”