Machine‐Driven Enzymatic Oligosaccharide Synthesis by Using a Peptide Synthesizer

Abstract

For decades, researchers have endeavored to develop a general automated system to synthesize oligosaccharides that is comparable to the preparation of oligonucleotides and oligopeptides by commercially available machines. Inspired by the success of automated oligosaccharide synthesis through chemical glycosylation, a fully automated system is reported for oligosaccharides synthesis through enzymatic glycosylation in aqueous solution. The designed system is based on the use of a thermosensitive polymer and a commercially available peptide synthesizer. This study represents a proof‐of‐concept demonstration that the enzymatic synthesis of oligosaccharides can be achieved in an automated manner using a commercially available peptide synthesizer.

Donor Preactivation‐Based Glycosylation: An Efficient Strategy for Glycan Synthesis

“…Advances have been made in automated assembly of complex oligosaccharides, including automated solid‐phase oligosaccharide synthesis, [ 79‐80 ] automated solution‐phase oligosaccharide synthesis, [ 81‐82 ] and enzyme‐modulated assembly of oligosaccharides. [ 83‐85 ] Towards this direction, the automated glycan synthesis by preactivation‐based glycosylation strategy will await investigation.…”

Preparation of Complex Glycans From Natural Sources for Functional Study

“…Chemoenzymatic approaches have been developed for the synthesis of structurally defined glycans in the last two decades (Koeller et al, 2000;Blixt and Razi, 2006;Boltje et al, 2009;Lepenies et al, 2010;Palcic, 2011;Schmaltz et al, 2011). A lot of effort and various synthetic methods have been introduced to make more complex glycans available (Wang et al, 2013(Wang et al, , 2018Chen, 2015;Li et al, 2015;Shivatare et al, 2016;Prudden et al, 2017;Zhang et al, 2017;Wen et al, 2018;Liu et al, 2019), and recently, two enzyme-mediated oligosaccharide synthesizers were reported to facilitate the synthetic progress (Zhang et al, 2018;Li et al, 2019). Despite many recent advancements in prototypic automated glycan synthesis, the synthesis of complex, highly branched glycan structures is still extremely challenging and can only be carried out in a number of noncommercialized laboratories.…”

Regeneration of Free Reducing Glycans from Reductive Amination-Tagged Glycans by Oxone

“…Because of recently developed analytical methods and technologies, such as high-resolution and specialized mass spectrometry (MS), high-performance liquid chromatography (HPLC), genetic and cell biological approaches, and glycan microarrays, it has become possible to explore glycan structures and functions more deeply. , However, one crucial barrier to the field is inadequate access to biomedically relevant and diverse complex glycan structures, which not only limits the development of analytical methods relying on structural standards but also directly limits the functional study of individual glycan structures. The synthesis of glycans has significantly improved along with the recent reports of the elegant synthesis of complex glycans and microwave/HPLC-assisted machine-driven glycan synthesis. − However, the synthesis of complex glycans is still challenging and laborious, which is practiced in only a limited number of highly specialized laboratories.…”