Synthetic study of 3-fluorinated sialic acid derivatives

Suzuki, Katsuhiko; Daikoku, Shusaku; Son, Sang-Hyun; Ito, Yukishige; Kanie, Osamu

doi:10.1016/j.carres.2014.12.010

Cited by 13 publications

(9 citation statements)

References 35 publications

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“…Various N-acyl derivatives of CMP-neuraminic acid have been prepared in 50-70% yield. CMP-activated neuraminic acid derivatives have been synthesized also by using phosphoramidite chemistry [166]. Fluorescently labeled derivatives have been prepared by coupling a nucleoside phosphoramidite building block and a protected sialic acid derivative with tetrazole as an activator [166].…”

Section: Chemical Synthesismentioning

confidence: 99%

Nucleotide Sugars in Chemistry and Biology

Mikkola

2020

Molecules

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Nucleotide sugars have essential roles in every living creature. They are the building blocks of the biosynthesis of carbohydrates and their conjugates. They are involved in processes that are targets for drug development, and their analogs are potential inhibitors of these processes. Drug development requires efficient methods for the synthesis of oligosaccharides and nucleotide sugar building blocks as well as of modified structures as potential inhibitors. It requires also understanding the details of biological and chemical processes as well as the reactivity and reactions under different conditions. This article addresses all these issues by giving a broad overview on nucleotide sugars in biological and chemical reactions. As the background for the topic, glycosylation reactions in mammalian and bacterial cells are briefly discussed. In the following sections, structures and biosynthetic routes for nucleotide sugars, as well as the mechanisms of action of nucleotide sugar-utilizing enzymes, are discussed. Chemical topics include the reactivity and chemical synthesis methods. Finally, the enzymatic in vitro synthesis of nucleotide sugars and the utilization of enzyme cascades in the synthesis of nucleotide sugars and oligosaccharides are briefly discussed.

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Section: Chemical Synthesismentioning

confidence: 99%

Nucleotide Sugars in Chemistry and Biology

Mikkola

2020

Molecules

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“…The driving force for the formation of a 2,3-dehydro derivative 24 might have been attributed to the presence of a destabilizing electron-withdrawing carboxy group flanking atom C-2 and the lack of a participating auxiliary in position C-3 of 5. Glycal 24 is widely used for α-sialylation by utilizing neighboring group participation and site-selective fluorination at C-3 [12][13][14]41]. Moreover, it is the main precursor in the synthesis of inhibitors for N-acetylneuraminidases from different sources [42].…”

Section: Resultsmentioning

confidence: 99%

SnCl₄-catalyzed solvent-free acetolysis of 2,7-anhydrosialic acid derivatives

Asressu

Wang

2019

Beilstein J. Org. Chem.

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Sialic acid-containing glycans are found in different sialic acid forms and a variety of glycosidic linkages in biologically active glycoconjugates. Hence, the preparation of suitably protected sialyl building blocks requires high attention in order to access glycans in a pure form. In line with this, various C-5-substituted 2,7-anhydrosialic acid derivatives bearing both electron-donating and -withdrawing protecting groups were synthesized and subjected to different Lewis acid-catalyzed solvent-free ring-opening reactions at room temperature in the presence of acetic anhydride. Among the various Lewis acids tested, the desired acetolysis products were obtained in moderate yields under tin(IV) chloride catalysis. Our methodology could be extended to regioselective protecting group installations and manipulations towards a number of thiosialoside and halide donors. 2990

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“…Cells treated with the sialic acid inhibitor 3FS decreased sialylation by approximately 60%. The sialic acid analog is incorporated into the salvage pathway and converted to the active form of the sugar by attaching CMP resulting in the nucleotide sugar CMP-3FS [ 31 , 32 ]. The active form of the sugar then inhibits the transferase, depleting the cells of sialylated glycans.…”

Section: Discussionmentioning

confidence: 99%

N-Glycomic Analysis of the Cell Shows Specific Effects of Glycosyl Transferase Inhibitors

Zhou

Xie

Lam

et al. 2021

Cells

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Glycomic profiling methods were used to determine the effect of metabolic inhibitors on glycan production. These inhibitors are commonly used to alter the cell surface glycosylation. However, structural analysis of the released glycans has been limited. In this research, the cell membranes were enriched and the glycans were released to obtain the N-glycans of the glycocalyx. Glycomic analysis using liquid chromatography–mass spectrometry (LC–MS) with a PGC chip column was used to profile the structures in the cell membrane. Glycans of untreated cells were compared to glycans of cells treated with inhibitors, including kifunensine, which inhibits the formation of complex- and hybrid-type structures, 2,4,7,8,9-Penta-O-acetyl-N-acetyl-3-fluoro-b-d-neuraminic acid methyl ester for sialylated glycans, 2-deoxy-2-fluorofucose, and 6-alkynyl fucose for fucosylated glycans. Kifunensine was the most effective, converting nearly 95% of glycans to high mannose types. The compound 6-alkynyl fucose inhibited some fucosylation but also incorporated into the glycan structure. Proteomic analysis of the enriched membrane for the four inhibitors showed only small changes in the proteome accompanied by large changes in the N-glycome for Caco-2. Future works may use these inhibitors to study the cellular behavior associated with the alteration of glycosylation in various biological systems, e.g., viral and bacterial infection, drug binding, and cell–cell interactions.

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Synthetic study of 3-fluorinated sialic acid derivatives

Cited by 13 publications

References 35 publications

Nucleotide Sugars in Chemistry and Biology

Nucleotide Sugars in Chemistry and Biology

SnCl₄-catalyzed solvent-free acetolysis of 2,7-anhydrosialic acid derivatives

N-Glycomic Analysis of the Cell Shows Specific Effects of Glycosyl Transferase Inhibitors

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Synthetic study of 3-fluorinated sialic acid derivatives

Cited by 13 publications

References 35 publications

Nucleotide Sugars in Chemistry and Biology

Nucleotide Sugars in Chemistry and Biology

SnCl4-catalyzed solvent-free acetolysis of 2,7-anhydrosialic acid derivatives

N-Glycomic Analysis of the Cell Shows Specific Effects of Glycosyl Transferase Inhibitors

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SnCl₄-catalyzed solvent-free acetolysis of 2,7-anhydrosialic acid derivatives