Expedited synthesis of mannose-6-phosphate containing oligosaccharides.

Currently, the reaction toolbox for the functionalization of glycans assembled on solid-phase is quite limited. Automated (1 h) and manual (overnight) phosphorylation protocols that enable the solid-phase synthesis of oligosaccharides containing up to two mannose-6-phosphates are presented. Automated glycan assembly expedited access to substrates and facilitated the screening of experimental conditions.

Microwave-Assisted Automated Glycan Assembly.

Automated synthesis of DNA, RNA, and peptides provides quickly and reliably important tools for biomedical research. Automated glycan assembly (AGA) is significantly more challenging, as highly branched carbohydrates require strict regio- and stereocontrol during synthesis. A new AGA synthesizer enables rapid temperature adjustment from -40 to +100 °C to control glycosylations at low temperature and accelerates capping, protecting group removal, and glycan modifications using elevated temperatures. Thereby, the temporary protecting group portfolio is extended from two to four orthogonal groups that give rise to oligosaccharides with up to four branches. In addition, sulfated glycans and unprotected glycans can be prepared. The new design reduces the typical coupling cycles from 100 to 60 min while expanding the range of accessible glycans. The instrument drastically shortens and generalizes the synthesis of carbohydrates for use in biomedical and material science.