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

PS2 Poster session 2 Even numbers
Location (hall): 
Start/end time: 
Tuesday, July 2, 2019 - 15:45 to 17:15

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.


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

  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.