My Stroll in the Backyard of Carbohydrate Chemistry

Ito, Yukishige

doi:10.4052/tigg.22.119

Cited by 8 publications

(3 citation statements)

References 96 publications

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“…Using synthetic glycans and their analogues, we conducted quantitative analysis of their specific interactions with lectins, chaperones, glycosidases and glycosyltransferases (7,8). The results of interaction analysis of CRT and Fbs1 quantified by isothermal titration calorimetry revealed that these proteins can distinguish small differences in the fine structure of glycans.…”

Section: Analysis For Gqc Related Protein Using N-glycan Probesmentioning

confidence: 99%

Toward Understanding <i>N</i>-Glycan Functions through Chemical Synthesis

Matsuo

2019

TIGG

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N-Glycosylation of secretory and membrane-bound proteins is an essential and highly conserved protein modification of eukaryotes. In the endoplasmic reticulum (ER), a combination of various enzymes, chaperones, lectins and cargo receptors constitutes the "glycoprotein quality control" (GQC) system, which elaborately regulates folding, transport and degradation of glycoproteins. Thus, function of asparagine linked sugar chains in the GQC process has been attracting attention. Understanding of these phenomena has progressed as a result of interaction analyses and substrate specificity studies of glycan related enzymes using synthetic sugar chains. In this review, our approach to the systematic synthesis of the ER type of asparagine linked sugar chains (N-glycans) and recent progress of this field is described.

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Section: Analysis For Gqc Related Protein Using N-glycan Probesmentioning

confidence: 99%

Toward Understanding <i>N</i>-Glycan Functions through Chemical Synthesis

Matsuo

2019

TIGG

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“…Several strategies for the synthesis of disaccharide nucleosides such as enzymatic O -glycosylation [ 20 , 21 ], chemical N -glycosylation [ 5 , 9 , 16 , 22 , 23 , 24 ] and chemical O -glycosylation [ 7 , 9 , 14 , 16 , 18 , 19 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 ] have been reported to date. Chemical O -glycosylation is often useful for the large-scale synthesis of the desired disaccharide nucleosides in higher chemical yields compared to chemical N -glycosylation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Disaccharide Nucleosides Utilizing the Temporary Protection of the 2′,3′-cis-Diol of Ribonucleosides by a Boronic Ester

2017

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Disaccharide nucleosides are an important class of natural compounds that have a variety of biological activities. In this study, we report on the synthesis of disaccharide nucleosides utilizing the temporary protection of the 2′,3′-cis-diol of ribonucleosides, such as adenosine, guanosine, uridine, 5-metyluridine, 5-fluorouridine and cytidine, by a boronic ester. The temporary protection of the above ribonucleosides permits the regioselective O-glycosylation of the 5’-hydroxyl group with thioglycosides using a p-toluenesulfenyl chloride (p-TolSCl)/silver triflate (AgOTf) promoter system to afford the corresponding disaccharide nucleosides in fairly good chemical yields. The formation of a boronic ester prepared from uridine and 4-(trifluoromethyl)phenylboronic acid was examined by 1H, 11B and 19F NMR spectroscopy.

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“…The content of this review article was inspired by an outstanding contribution by Dr. Yukishige Ito, who has recently published a review in the same Journal (1). This review is primarily dedicated to contributions from our laboratory (The Glycoworld) into the field of glycosciences, which are discussed in the context of other advancements in the field of chemical synthesis with carbohydrates.…”

Section: A Introductionmentioning

confidence: 99%