Synthesis and immunochemical studies of linear oligoglucosides structurally related to the cyclic β-(1→2)-d-glucan of Brucella

Synthesis and immunochemical studies of linear oligoglucosides structurally related to the cyclic β-(1→2)-d-glucan of Brucella Full article

Journal

Communications Chemistry
ISSN: 2399-3669

Output data

Year: 2025, Volume: 8, Number: 1, Article number : 172, Pages count : DOI: 10.1038/s42004-025-01570-7

Authors

Kuznetsov Anton N ¹ , Gerbst Alexey G ² , Tsvetkov Yury E ² , Khodzhibekov Rasim R ³ , Dalgatova Asiyat A ³ , Burgasova Olga A ^3,4 , Kulakov Yury K ⁴ , Krylov Vadim B ¹ , Nifantiev Nikolay E ²

Affiliations

1	Laboratory of Synthetic Glycovaccines, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation.
2	Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation.
3	Department of Infectious Diseases, Peoples' Friendship University of Russia (RUDN University), Moscow, Russian Federation.
4	Laboratory of Brucellosis and Natural Focal Infections, National Research Centre for Epidemiology and Microbiology named after honorary academician N. F. Gamaleya of the Ministry of Health of the Russian Federation, Moscow, Russian Federation.

Cyclic β-(1→2)-d-glucan (CβG) is a unique carbohydrate derivative produced by pathogenic bacteria of the genus Brucella. Controversial opinions regarding the use of CβG in brucellosis diagnosis have been published. Herein we report the first synthesis of spacered oligo-β-(1→2)-d-glucosides related to the fragments of CβG and containing up to 5 glucose units. Although the desired di- and trisaccharides could be obtained using standard methods, the synthesis of tetra- and pentasaccharides required substantial effort. The obtained oligosaccharides exhibited complex dependencies of their NMR spectral data on the chain length, explained by a tendency to form helical structures. Despite high production of the CβG by Brucella, antibodies to β-(1→2)-d-glucosides detected in human sera are not related to the brucellosis. However, the antibodies to CβG were raised after immunization by BSA-conjugate of penta-β-(1→2)-d-glucoside and allowed detection of CβG, which opens a way towards the development of the new brucellosis diagnostic kit.

Kuznetsov A.N. , Gerbst A.G. , Tsvetkov Y.E. , Khodzhibekov R.R. , Dalgatova A.A. , Burgasova O.A. , Kulakov Y.K. , Krylov V.B. , Nifantiev N.E.
Synthesis and immunochemical studies of linear oligoglucosides structurally related to the cyclic β-(1→2)-d-glucan of Brucella
Communications Chemistry. 2025. V.8. N1. 172 . DOI: 10.1038/s42004-025-01570-7 WOS Scopus OpenAlex

≡ Web of science:	WOS:001502184200001
≡ Scopus:	2-s2.0-105007543400
≡ OpenAlex:	W4411010252