The first part of my talk centers on the application of cation clock reactions for the determination of relative reaction kinetics in sialidation reactions. The formation of glycosidic bonds is perhaps the most important bond forming reaction in glycoscience, playing a critical role in the assembly of all glycoconjugates. In general, the control of the glycosylation reaction is a key ingredient to engineering better stereoselective oligosaccharide synthesis irrespective of the assembly strategy used.

Glycosylation reactions stereoselectivity depends on various factors and among them, side-chain configuration and conformation have been showing significant roles in influencing the reactivity and selectivity in bicyclic glycosyl donors. Moving to monocyclic donors, this effect has been revealed in glycosylation reactions of sialic acid donor series and simple pyranoside series. We studied the extension of this concept towards furanosides by synthesizing two suitably protected epimers of 5-methyl-D-xylose from D-xylose.

Carbohydrates are the most abundant class of molecules in the biosphere. Glycosylated secondary metabolites play a major role in carbohydrate chemistry expanding the scope of potential drug motifs. Glycosylated natural products are made out of sugars covalently O-, C-, N- or S- linked to the aglycone counterpart. In the course of synthesizing potential glycosidic therapeutics, effective and straightforward regio and stereoselective glycosylation methods are in high demand.

Per- and Polyfluoroalkyl substances (PFAS’s) are widely used to coat paper and cardboard for food packaging because of their desirable grease, water, and heat resistant properties.

The first half of the talk focuses on aminoglycoside antibiotics, highly active protein synthesis inhibitors that impact a wide range of both Gram positive and Gram negative bacteria. Though these drugs have many benefits and currently find use in the clinic, they can bring about reversible nephrotoxicity and irreversible ototoxicity.

Over the years, a common obstacle put in front of chemists has been the ability to construct molecules with medium sized ring structure in a high yielding and selective fashion. These higher order cyclic systems have a variety of problems synthetically with low levels of regioselective, chemoselectivity, stereoselectivity, and high levels of strain inside the scaffolds. There are very few examples of larger than six-membered rings easily synthesized using classic cycloaddition methods such as Diels-Alder and variants thereof.

Sulfur-fluoride exchange (SuFEx) reaction was first demonstrated by Sharpless and his co-workers¹ in 2014. SuFEx is now considered as the second generation of click chemistry. It was established on the silicon centers, which can activate the exchange of S-F bonds for S-O bonds. A strong base, like triazabicyclodecene (TBD), was usually considered as the catalyst of SuFEx. Since then, we started to explore the possibility of the reaction between other heteroatom fluorides and silyl ethers. We found boron-fluoride (B-F) bonds are reactive as well.

In 1963 solid-phase peptide synthesis (SPPS) was introduced by Merrifield. Since then, the chemical synthesis of short peptides became routine. However, synthesis of long peptides remains difficult, being time demanding and offering lower yields as the size of the desired chain increases. Likewise, the synthesis of small proteins was not possible until the development of Native Chemical Ligation (NCL), a technique for ligation of peptides to produce longer polypeptides/proteins.