The results of studies of the glycosylation reactions mechanism carried out at the ZIOC are placed on the cover of a highly rated journal

Sialic acids are nine-carbon monosaccharides with a carboxyl group at the C-2 anomeric center and a flexible side chain at the C-6 atom. Glycoconjugates containing these structures are the key participants in carbohydrate-protein interactions that are realized during many biological processes, ranging from cell motility and adhesion, recognition by viruses and bacteria to the immune response and oncogenesis. In synthetic chemistry, sialic acids are added to other carbohydrates through a glycosylation reaction. Understanding the mechanism of such processes is an important scientific task necessary to gain control over the result of the reaction and, therefore, to obtain the desired anomer.

Researchers from the Laboratory of Glycochemistry of the ZIOC have developed a new approach to study the conformational space of the sialyl cation and found 1625 unique conformers of this key intermediate in the glycosylation reaction. As a result of the analysis of the obtained results, a hypothesis was formulated that describes the mutual transformations of the most important conformers of the sialyl cation. It was concluded that a more effective participation of remote acyl groups promotes the formation of β-anomers, and the selective synthesis of α-sialosides requires the minimization of the participation of acyl groups.

The results of this study are featured on the cover of a recent issue of the prestigious international journal ChemPhysChem.

Source:

Maria V. Panova, Michael G. Medvedev, Anna V. Orlova, Leonid O. Kononov Exhaustive Conformational Search for Sialyl Cation Reveals Possibility of Remote Participation of Acyl Groups ChemPhysChem 2022, e202100788. DOI: 10.1002/cphc.202100788.