Convergent Synthesis of Oligosaccharides Structurally Related to Galactans of Klebsiella Pneumoniae and Their Use in Screening of Antibody Specificity

Session: 
PS2 Poster session 2 Even numbers
Code: 
P8
Location (hall): 
Foyer
Start/end time: 
Tuesday, July 2, 2019 - 15:45 to 17:15
D.A.
Argunov

D.A. Argunov1, V.B. Krylov1, N.E. Nifantiev1

1Laboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russia

Klebsiella pneumoniae is a Gram-negative pathogenic bacterium that emerges a challenge for modern medicine due to intensively rising multi-drug resistance. Polysaccharides linked to the core region of LPS O-chains represent promising targets for development vaccines for immunoprophylaxis or immunotherapy of K. pneumoniae-caused diseases. The O-antigens of the most prevalent O1 serotype are built up from galactan I, galactan II and galactan III.

Herein we report the synthesis of biotinylated 2-,4- and 6-saccharides 1‑6 structurally related both to galactan I and galactan II (scheme 1). For the assembling of target oligosaccharides convergent strategy based on disaccharide donors 9 and 11 was used. The key step for preparation of galactofuranose-containing synthetic blocks was pyranoside-into-furanoside (PIF) rearrangement [1].

Biotinylated oligosaccharides 1-6 were immobilized on the surface of streptavidin coated plates to form glycoarray which was applied for screening of sera against K. pneumoniae. The obtained results demonstrate the applicability of such a glycoarray-based assay for typing Klebsiella strains belonging to most frequent O1 serogroup [2].

Scheme 1. Key blocks and stages in the synthesis of galactan I and galactan II related oligosaccharides.

Acknowlegements

This work was supported by RSF grant 19-73-30017.

References: 
  1. V.B. Krylov, D.A. Argunov, D.Z. Vinnitskiy, S.A. Verkhnyatskaya, A.G. Gerbst, N.E. Ustyuzhanina, A.S. Dmitrenok, J. Huebner, O. Holst, H.-C. Siebert, N.E. Nifantiev, Chem. Eur. J., 2014, 20, 16516-16522.
  2. D.A. Argunov, A.S. Trostianetskaia, V.B. Krylov, E.A. Kurbatova, N.E. Nifantiev, Eur. J. Org. Chem., 2019, in press.

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