The results of studies of glycosylation reactions in flow reactors carried out in ttheZelinsky Institute are placed on the cover of the international journal

Glycosylation reaction is very important in the chemical synthesis of natural glycans and glycoconjugates.It plays a key role in many biological processes, ranging from cell motility and adhesion, interaction with viruses and bacteria, to immune response and oncogenesis. Understanding the mechanism of glycosylation is an important scientific task necessary to control the outcome of the reaction.

Researchers of the Laboratory of Glycochemistry of the ZIOC found that the stereoselectivity of glycosylation can change if different methods of mixing reagents are used. Conducting the reaction in flow with more efficient mixing and, therefore, better mass transfer led not only to the expected increase in product yield compared to the reaction in batch, but also to an unexpected decrease in stereoselectivity: the formation of both anomers of glycosides — derivatives of sialic acids was observed, which indicates change in the mechanism of this process. The result was found to depend on the nature of the glycosyl acceptor, the type of flow micromixer used, and the flow rate.

To rationally explain the unexpected formation of an anomeric mixture, the scientists proposed a model based on the suprameric concept of reactivity developed at the Laboratory of Glycochemistry, which is based on the hypothesis that the true participants in chemical reactions in solutions are long-lived supramolecular structures (supramers) that include molecules of reagents.

The results of this study are featured on the cover of a recent issue of the prestigious international journal European Journal of Organic Chemistry.

Source:

Ilya V. Myachin, Zarina Z. Mamirgova, Elena V. Stepanova, Alexander I. Zinin, Alexander O. Chizhov, Leonid O. Kononov. Black Swan in Phase Transfer Catalysis: Influence of Mixing Mode on the Stereoselectivity of Glycosylation. Eur. J. Org. Chem. 2022, e202101377. DOI: 10.1002/ejoc.202101377.