Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

Abstract

Advances in carbohydrate chemistry have certainly made common oligosaccharides much more accessible. However, many current methods still rely heavily upon specialized knowledge of carbohydrate chemistry. The application of automated technologies to chemical and life science applications such as genomics and proteomics represents a vibrant field. These automated technologies also present opportunities for their application to organic synthesis, including that of the synthesis of oligosaccharides. However, application of automated methods to the synthesis of carbohydrates is an underdeveloped area as compared to other classes of biomolecules. The overarching goal of this review article is to present the advances that have been made at the interface of carbohydrate chemistry and automated technology.

Unraveling the isomeric heterogeneity of glycans: ion mobility separations in structures for lossless ion manipulations

“…Glycans are one of the most ubiquitous biomolecules, where their specific structures dictate myriad biological and pathological functions in plants, fungi, mammals, and bacteria 1 . As compared to other biomolecules (e.g., nucleic acids, peptides), glycan synthesis is performed in a non-template driven fashion, where their composition can be varied according to immunological responses, cellular signaling, and disease state 1 .…”

“…As compared to other biomolecules (e.g., nucleic acids, peptides), glycan synthesis is performed in a non-template driven fashion, where their composition can be varied according to immunological responses, cellular signaling, and disease state 1 . This variation in glycan composition, termed isomeric heterogeneity, leads to numerous potential structural permutations (e.g., regioisomers, stereoisomers, and diastereomers), further complicating analyses 2 .…”

“…Currently, the most commonly used analytical technique for glycan separations is liquid chromatography coupled to tandem mass spectrometry (LC-MS/MS) 1 , 4 . Chemical derivatization is often a prerequisite for reversed-phase separations so as to increase the hydrophobicity of the inherently polar glycans 1 , 2 .…”

“…Chemical derivatization is often a prerequisite for reversed-phase separations so as to increase the hydrophobicity of the inherently polar glycans 1 , 2 . While reversed-phase separations remain the preferred choice in glycan separations, HILIC or normal stationary phases have seen some recent use 2 .…”

Carbohydrate‐based nanomaterials for biomedical applications

“…Nevertheless, for simplicity, most glycosylated‐materials are based on a synthetic scaffold functionalized with multiple copies of simple mono‐ or oligosaccharides. Such molecules can be prepared by chemical synthesis and/or enzymatic methods, obtaining well‐defined structures (Kadokawa, ; Panza, Pistorio, Stine, & Demchenko, ; Pardo‐Vargas, Delbianco, & Seeberger, ); unnatural structures are also accessible through chemical modifications. As an alternative to synthetic compounds, polysaccharides extracted from natural sources offer a valuable substrate for the formation of materials (Garcia‐Vaquero, Rajauria, O'Doherty, & Sweeney, ; Ruthes, Smiderle, & Iacomini, ).…”