Oligosaccharide Synthesis on Solid, Soluble Polymer, and Tag Supports

HPLC-Assisted Automated Oligosaccharide Synthesis: Implementation of the Autosampler as a Mode of the Reagent Delivery

“…This mismatch is typically addressed by using a large excess (5–10 equiv) of the solution-based reactant, most commonly the donor, and repeating the reaction 2–3 times to ensure that all solid-supported acceptor is consumed. 14 Automation offers some operational simplicity to oligosaccharide synthesis, but the entire concept may suffer from the inherited drawbacks of conventional methods.…”

“…Solid-phase synthesis, , which eliminates the need for purifying intermediates and simplifies the removal of excess reagents, has been widely used in the preparation of peptides , and oligonucleotides . Since 1971, solid-phase synthesis has been used for the preparation of oligosaccharides; − and in 2001 Seeberger et al reported the first automated oligosaccharide synthesis using a modified peptide synthesizer. − In 2012, Seeberger et al reported “the first fully automated solid-phase oligosaccharide synthesizer,” initially in its experimental form; and in 2013 it was marketed as Glyconeer 2.1. Approaches by Wong, , Takahashi, , Chen, − Pohl, − Wang, , and Nokami , are based on the automation of chemical, enzymatic, or chemoenzymatic syntheses in solution with or without using tags …”

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

“…This method has emerged to address problems of the resin-supported synthesis associated with slow reactions and reactivity mismatch between unreactive solid-phase based and highly reactive solution-based reactants. 474,475 These supports, and everything attached to it, are freely soluble in the reaction media but could be precipitated by the addition of diethyl ether or other suitable solvent and recovered by filtration. 476–478 Alternatively, nanofiltration or a size-exclusion separation offer other possible alternatives for separation of polymer-bound molecules and the rest of the reaction components.…”

Immobilization of glycans on solid surfaces for application in glycomics

“…[63–65] By eliminating or simplifying intermediate steps such as work-up and purification, solid-phase oligosaccharide synthesis streamlines access to pure quantities of specific oligosaccharide sequences. [66–70] Synthesis on solid phase has also opened the door to automation of oligosaccharide synthesis for the purpose of producing glycans of interest and making them readily accessible to researchers. [71–74] One such potential application of carbohydrate synthesis is in oncology.…”