Convergent Synthesis of Oligosaccharides Structurally Related to Galactan I and Galactan II of Klebsiella Pneumoniae and their Use in Screening of Antibody Specificity

Abstract

Klebsiella pneumoniae Is a Gram‐negative pathogenic bacterium that emerges a challenge for modern medicine due to intensively rising multi‐drug resistance. Specific LPS O‐chains represent promising targets for development of vaccines for immunoprophylaxis or immunotherapy of K. pneumoniae‐caused diseases. Herein, the synthesis of di‐, tetra‐, and hexasaccharides which represent structural fragments of both galactan I and galactan II of K. pneumoniae LPS O‐chains is described. The galactofuranoside building block used for assembling the galactan I chains was prepared by pyranoside‐into‐furanoside (PIF) rearrangement of the corresponding galactopyranoside precursor bearing an acid‐labile temporary p‐methoxybenzyl protecting group at O(3). The synthesized set of K. pneumoniae antigenic oligosaccharides in the form of their biotinylated derivatives was used to create a glycoarray which was applied for the screening of antibodies to galactan I and galactan II in anti‐K. pneumoniae sera. The obtained results demonstrate the applicability of such a glycoarray‐based assay for typing antibodies to Klebsiella strains belonging to most frequent O1 serogroup.

Importance of Candida Antigenic Factors: Structure-Driven Immunomodulation Properties of Synthetically Prepared Mannooligosaccharides in RAW264.7 Macrophages

“…Next, a novel tetrasaccharide construct consisting of β-1,2-mannopyranosyl trisaccharide and α-mannopyranoside was designed and suggested as a model of the C. albicans phosphodiester epitope (Dang et al, 2012). Glycoarrays formed by biotinylated oligosaccharides loaded on streptavidin-coated surfaces were previously shown to be indispensable instruments for the investigation of carbohydrate antigen recognition by immune cells (Komarova et al, 2015, 2018; Akhmatova et al, 2016; Paulovicova et al, 2016, 2017; Kurbatova et al, 2017; Argunov et al, 2019; Schubert et al, 2019).…”

Reinvestigation of Carbohydrate Specificity of EBCA-1 Monoclonal Antibody Used for the Detection of Candida Mannan

“…Modern methods of carbohydrate chemistry permit efficient and stereospecific assembling of complex oligosaccharide chains representing different parts of polysaccharides of the fungal cell wall [ 22 , 23 , 24 ]. The arrays of oligosaccharides (glycoarrays) were shown to be indispensable tools in the assessment of ligand specificity of anti-carbohydrate monoclonal antibodies [ 25 , 26 , 27 , 28 , 29 , 30 , 31 ] and of antibodies in the blood sera [ 26 , 32 , 33 , 34 ].…”

Synthetic Analogs of Streptococcus pneumoniae Capsular Polysaccharides and Immunogenic Activities of Glycoconjugates

“…Extensive research in this area has made it possible to create certain algorithms for the efficient selection of the most active carbohydrate ligands. Modern methods allow automated screening of carbohydrate ligands using on-chip carbohydrate arrays [54,59,62] and other carriers [139][140][141][142][143][144][145] to study epitope specificity of the tested antibodies. New efficient methods for synthesis of the most complex types of oligosaccharides have also been developed (see, for example, [146][147][148][149]), including the automated synthesis of oligosaccharides [150,151], which significantly simplifies preparation of extended libraries of the carbohydrate ligands.…”