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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.
This article was published in the following journal.
Name: Journal of the American Chemical Society
A simple and direct DMF-modulated α-selective Kdo glycosylation approach for the stereoselective synthesis of the α-linked Kdo glycosides is developed. Glycosylation of the readily available peracet...
An intramolecular glycosylation strategy was used to synthesize a series of new glycoazobenzene macrocycles with high α-selectivity and interesting chiroptical properties. The photoisomerization of a...
Poly(hydroxy acid)s are a family of biocompatible and (bio)degradable polyesters with various outcomes in different domains of application. To date, poly(hydroxy acid)s are best prepared by ring-openi...
The development of novel ligands specifically tailored for homogeneous gold catalysis permits the development of new gold catalysis. In this work, we report that a remotely functionalized biphenyl-2-y...
Our previous study showed that picoloylated donors are capable of providing excellent facial stereoselectivity via the H-bond-mediated aglycone delivery (HAD) pathway. Presented herein is a detailed m...
The goal of this study is to better characterize the metabolic alterations and sugar structure alterations (glycosylation abnormalities) in patients diagnosed with Congenital Disorders of ...
Researchers are trying to assess whether the use of simple sugars given as a daily dietary supplement can improve the health of children with congenital disorders of glycosylation (CDG).
The purpose of this research is to study the natural history of congenital disorders of glycosylation and its causes and treatments.
Primary objectives: 1. To comprehensively characterize steady state stereoselective pharmacokinetics of bupropion and its primary and secondary metabolites in healthy volunteers ...
The purpose of this study is to investigate the coagulation balance in a cohort of congenital disorder of glycosylation (CDG) patients using conventional tests combined with an integrated ...
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.
A genetically heterogeneous group of heritable disorders resulting from defects in protein N-glycosylation.
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.
A diagnostic test is any kind of medical test performed to aid in the diagnosis or detection of disease. For example: to diagnose diseases to measure the progress or recovery from disease to confirm that a person is free from disease Clin...