Institute of Organic Chemistry of the Russian Academy of Sciences conducts Research on the synthesis of fragments of the tuberculosis pathogens cell wall are conductd in the Zelinsky Institute

Mycobacterial infections caused by bacteria of the genus Mycobacteria, and in particular by the microorganism Mycobacterium tuberculosis, the main causative agent of tuberculosis, attract considerable attention from scientists from various fields of science due to the growing incidence of tuberculosis worldwide. An important structural component of the cell wall of mycobacteria is the polysaccharide lipoarabinomannan (LAM), which is the main non-protein antigen of mycobacteria and plays an important role in the pathogenesis of tuberculosis. For this reason, in recent years, more and more attention has been paid to the development of diagnostic tools based on LAM and its fragments.

Scientists from the Laboratory of Glycochemistry of the ZIOC in one of their recent papers studied the formation of a 1,2-trans-arabinofuranoside bond in arabinan fragments of LAM. Glycosylation with a 1,2-cis-linked disaccharide glycosyl donor based on arabinofuranose without co-stereodirecting group at O-2, has been shown to be stereospecific using bulky triisopropylsilyl groups to protect all five hydroxyl groups of the glycosyl donor. The results obtained open up prospects for the development of new effective methods for the synthesis of oligosaccharide fragments of LAM, which are necessary for the development of tools for rapid diagnosis of tuberculosis.

The article published on the results of the study in European Journal of Organic Chemistry was assigned VIP status.

Source:

Polina I. Abronina, Nelly N. Malysheva, Elena V. Stepanova, Julia S. Shvyrkina, Alexander I. Zinin, Leonid O. Kononov Five Triisopropylsilyl Substituents in Ara-β-(1→2)-AraDisaccharide Glycosyl Donor Make Unselective Glycosylation Reaction Stereoselective // Eur. J. Org. Chem. 2022, e202201110. DOI: 10.1002/ejoc.202201110.