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Fluoride Migration Catalysis Enables Simple, Stereoselective, and Iterative Glycosylation.

08:00 EDT 24th March 2020 | BioPortfolio

Summary of "Fluoride Migration Catalysis Enables Simple, Stereoselective, and Iterative Glycosylation."

Challenges in the assembly of glycosidic bonds in oligosaccharides and glycoconjugates pose a bottleneck in enabling the remarkable promise of advances in the glycosciences. Here, we report a strategy that applies unique features of highly electrophilic boron catalysts, such as tris(pentafluorophenyl)borane, in addressing a number of the current limitations of methods in glycoside synthesis. This approach utilizes glycosyl fluoride donors and silyl ether acceptors while tolerating the Lewis basic environment found in carbohydrates. The method can be carried out at room temperature using air- and moisture stable forms of the catalyst, with loadings as low as 0.5 mol %. These characteristics enable a wide array of glycosylation patterns to be accessed, including all C1-C2 stereochemical relationships in the glucose, mannose and rhamnose series. This method allows one-pot, iterative glycosylations to generate oligosaccharides directly from monosaccharide building blocks. These advances enable the rapid and experimentally straightforward preparation of complex oligosaccharide units from simple building blocks.

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This article was published in the following journal.

Name: Journal of the American Chemical Society
ISSN: 1520-5126
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Medical and Biotech [MESH] Definitions

Calcium fluoride. Occurring in nature as the mineral fluorite or fluorspar. It is the primary source of fluorine and its compounds. Pure calcium fluoride is used as a catalyst in dehydration and dehydrogenation and is used to fluoridate drinking water. (From Merck Index, 11th ed)

A source of inorganic fluoride which is used topically to prevent dental caries.

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Poisoning that results from chronic or acute ingestion, injection, inhalation, or skin absorption of FLUORIDE compounds.

Inorganic fluorides of tin. They include both stannic fluoride (tin tetrafluoride) and stannous fluoride (tin difluoride). The latter is used in the prevention of dental caries.

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