Synthesis of (1→4)-Linked 2-Deoxy-2-fluoroglucose Oligomers. 1

Sugiyama, Shin; Haque, Wasim; Diakur, James

doi:10.1021/ol006529i

Cited by 8 publications

(1 citation statement)

References 21 publications

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“…Indeed, there are only very few examples of such oligosaccharides. [27][28][29][30][31][32][33] Target trisaccharides 1-4 were constructed through a chemoenzymatic strategy (Scheme 1) by using parallel routes (Schemes 2-5); four variant Gal-GlcNAc intermediate disaccharides 5-8 containing different substituents F/OH or different connectivities bA C H T U N G T R E N N U N G (1,4)/bA C H T U N G T R E N N U N G (1,3) were accessed through chemical glycosylation by using trichloroacetimidate (TCA) donors 9 [34] and 10 [35] (Scheme 4). These, in turn, were converted into target trisaccharides 1-4 by using regio-and stereo-A C H T U N G T R E N N U N G selective T. cruzi transsialidase (TcTS)-catalysed glycosylation (Scheme 5).…”

Section: Synthetic Strategymentioning

confidence: 99%

Potent Fluoro‐oligosaccharide Probes of Adhesion in Toxoplasmosis

et al. 2009

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Unnatural, NMR- and MRI-active fluorinated sugar probes, designed and synthesised to bind to the pathogenic protein TgMIC1 from Toxoplasma gondii, were found to display binding potency equal to and above that of the natural ligand. Dissection of the binding mechanism and modes, including the first X-ray crystal structures of a fluoro-oligosaccharide bound to a lectin, demonstrate that it is possible to create effective fluorinated probe ligands for the study of, and perhaps intervention in, sugar-protein binding events.

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Section: Synthetic Strategymentioning

confidence: 99%

Potent Fluoro‐oligosaccharide Probes of Adhesion in Toxoplasmosis

et al. 2009

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Neue Prinzipien für die Bildung von glycosidischen Bindungen

2009

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Die wichtige Rolle, die Oligosaccharide und Glycokonjugate in biologischen Systemen spielen, erfordert immer neue und vor allem größere Mengen dieser Moleküle. Wegen ihrer Heterogenität in natürlichen Vorkommen wurden und werden große Anstrengungen unternommen, um die entscheidende glycosidische Bindung sowohl zwischen einzelnen Kohlenhydratresten als auch zu Aglyconen stereoselektiv und in hoher Ausbeute zu erzeugen. Es existieren nun verschiedene Methoden, die effiziente Synthesen von strukturell definierten komplexen Oligosacchariden und Glycokonjugaten ermöglichen. Das zunehmende Wissen um die bedeutende Rolle, die Oligosaccharide und Glycokonjugate in biologischen Prozessen spielen, hat rasch das Interesse an solchen Verbindungen für biologische, medizinische und pharmakologische Studien geweckt. Deshalb wurden und werden große Anstrengungen unternommen, um neue Methoden für die Synthese von Glycosiden zu entwickeln, wobei das Hauptaugenmerk auf die Bildung der glycosidischen Bindung gerichtet ist. Etliche Übersichtsartikel wurden in den letzten Jahren zur Glycosidsynthese verfasst, die meisten waren jedoch auf einen bestimmten Typ von Glycosiden oder eine bestimmte Methode zur Glycosidsynthese ausgerichtet. In diesem Aufsatz werden neue Prinzipien für die Bildung von glycosidischen Bindungen diskutiert, indem vor allem Arbeiten aus den letzten zehn Jahren berücksichtigt werden, die zu erheblichen Fortschritten in der Oligosaccharid‐ und Glycokonjugatsynthese geführt haben.

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New Principles for Glycoside‐Bond Formation

2009

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Increased understanding of the important roles that oligosaccharides and glycoconjugates play in biological processes has led to a demand for significant amounts of these materials for biological, medicinal, and pharmacological studies. Therefore, tremendous effort has been made to develop new procedures for the synthesis of glycosides, whereby the main focus is often the formation of the glycosidic bonds. Accordingly, quite a few review articles have been published over the past few years on glycoside synthesis; however, most are confined to either a specific type of glycoside or a specific strategy for glycoside synthesis. In this Review, new principles for the formation of glycoside bonds are discussed. Developments, mainly in the last ten years, that have led to significant advances in oligosaccharide and glycoconjugate synthesis have been compiled and are evaluated.

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Synthesis of (1→4)-Linked 2-Deoxy-2-fluoroglucose Oligomers. 1

Cited by 8 publications

References 21 publications

Potent Fluoro‐oligosaccharide Probes of Adhesion in Toxoplasmosis

Potent Fluoro‐oligosaccharide Probes of Adhesion in Toxoplasmosis

Neue Prinzipien für die Bildung von glycosidischen Bindungen

New Principles for Glycoside‐Bond Formation

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