Rational optimization of the mannoside building block for automated electrochemical assembly of the core trisaccharide of GPI anchor oligosaccharides

Manmode, Sujit; Sato, Takumi; Sasaki, Norihiko; Notsu, Ikumi; Hayase, Shuichi; Nokami, Toshiki; Itoh, Toshiyuki

doi:10.1016/j.carres.2017.08.009

Cited by 27 publications

(10 citation statements)

References 16 publications

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“…[ 78 ] It is also a hot topic in the field of oligosaccharide 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.…”

Section: Discussionmentioning

confidence: 99%

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

Qin

2021

Chin. J. Chem.

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Carbohydrates have gained a lot of appreciation in the past few decades due to their important roles in numerous biological events. Acquiring a structurally well‐defined carbohydrate compound is essential for the understanding of its functions. Although some innovative methods have been developed for the synthesis of complex oligosaccharides, glycan synthesis is in general still a time‐consuming and difficult work. Herein, we will introduce the preactivation‐based glycosylation strategy, which is an efficient protocol independent of the reactivity of glycosyl donor. This review will focus on summarizing the versatile applications of preactivation strategy in stereoselective glycosylation and one‐pot assembly of biologically important oligosaccharides and even polysaccharides. What is the most favorite and original chemistry developed in your research group? Preactivation‐based one‐pot glycosylation strategy and applications. How do you get into this specific field? Could you please share some experiences with our readers? I got into this field when I was a research associate in 1996. My supervisor, Prof. Chi‐Huey Wong, gave me a research topic for synthesis of oligosaccharide libraries. At that moment, as a beginner, I did not know too much carbohydrate chemistry, just to learn and to do it. The importance and challenge of carbohydrates attracted me. What is the most important personality for scientific research? Curiosity, passion, and creative thinking. How do you supervise your students? In my opinion, before the graduate students start a specific project, their experimental skills need to be well trained. During the period of graduate studies, the enhancement of abilities to analyze problems and to solve problems is very important. The graduate students should always keep an eye on the unusual experimental phenomena. What's your hobbies? Reading history books. What is your favorite journals? The journals publishing the latest research works in chemistry and medical science.

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Section: Discussionmentioning

confidence: 99%

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

Qin

2021

Chin. J. Chem.

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“…Another molecule of interest was a GPI anchor core trisaccharide, an oligomannoside of interest to show the advantages of novel strategies for oligosaccharide synthesis. 581 The study started with the evaluation of the oxidation potential of different building blocks, all characterized by a participating group at the C-2 or the C-6, such as acetyl or pivaloyl. The studied compounds were compared to the 4-fluorophenyl 2,3,4,6-tetra- O -benzyl-1-thio- α - d -mannopyranoside, and to better understand the changes in the potential, DFT calculations were performed.…”

Section: Automated Synthesis Of Oligosaccharidesmentioning

confidence: 99%

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

et al. 2018

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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.

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“…During our study of electrochemical glycosylation, we developed automated electrochemical assembly a method for the automated electrochemical solution‐phase synthesis of oligosaccharides. The method has already been successfully applied to the synthesis of linear oligoglucosamines, TMG‐Chitotriomycin, GPI anchor trisaccharides and 1,3‐1,6‐β‐linked oligoglucosides . Thus, we envisioned that precursors of cyclic oligosaccharides, especially oligoglucosamines, could also be readily prepared using this method, and that subsequent electrochemical glycosylation might be an alternative method for the chemical and enzymatic synthesis of cyclic oligosaccharides.…”

Section: Optimization Of Monosaccharide Terminal Building Blockmentioning

confidence: 99%

Electrochemical Glycosylation as an Enabling Tool for the Stereoselective Synthesis of Cyclic Oligosaccharides

et al. 2019

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Electrochemical glycosylation of a linear oligosaccharide with a protecting‐group‐free primary hydroxyl group afforded cyclic oligo‐saccharides, up to hexasaccharides, in high yields. Precursors of the cyclic oligosaccharides were prepared by automated electro‐chemical assembly‐a method for the automated electrochemical solution‐phase synthesis of oligosaccharides. We demonstrated that electrochemical glycosylation is useful not only for intermolecular glycosylation but also for intramolecular glycosylation to synthesize cyclic oligosaccharides.

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Rational optimization of the mannoside building block for automated electrochemical assembly of the core trisaccharide of GPI anchor oligosaccharides

Cited by 27 publications

References 16 publications

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

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

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

Electrochemical Glycosylation as an Enabling Tool for the Stereoselective Synthesis of Cyclic Oligosaccharides

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