Abstract: Brucellosis is a dangerous zoonotic disease caused by bacteria of the genus Brucella. Diagnosis of brucellosis is based on the detection in animal and human sera of antibodies to the O-polysaccharide of Brucella lipopolysaccharide. The currently employed serodiagnosis of brucellosis relies on the use of the Brucella O-polysaccharide as a diagnostic antigen. However, the existence of bacterial species, which also express O-polysaccharides structurally similar to that of Brucella, may decrease the specificity of the brucellosis detection due to false-positive test results. It has been shown that the efficiency of the test can be significantly improved by using synthetic oligosaccharides that correspond to the so-called M epitope of the Brucella O-antigen. This epitope is characterized by an α-(1→3)-linkage between d-perosamine units and is unique to Brucella. Here we report on an efficient approach to the synthesis of oligosaccharides that model the M epitope of the Brucella O-polysaccharide. The approach is based on the use of the α-(1→3)-linked disaccharide thioglycoside as the key donor block. Its application allowed the straightforward assembly of a set of four protected oligosaccharides, which includes a disaccharide, two trisaccharides, and a tetrasaccharide, in five glycosylation steps. The synthesized oligosaccharides are planned to be used in the development of diagnostic tools for identifying brucellosis in humans and domestic animals, as well as a potential vaccine against it.

Cite: Tsvetkov Y.E. , Volkov T.M. , Eremin S.A. , Sklyarov O.D. , Kulakov Y.K. , Krylov V.B. , Nifantiev N.E.
New synthesis of oligosaccharides modelling the M epitope of the Brucella O-polysaccharide
Frontiers in Chemistry. 2024. V.12. 1424157 . DOI: 10.3389/fchem.2024.1424157 WOS Scopus OpenAlex

Identifiers:

≡ Web of science:	WOS:001263089800001
≡ Scopus:	2-s2.0-85197556225
≡ OpenAlex:	W4399900915

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