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

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

Журнал

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Вых. Данные

Год: 2019, Том: 2019, Номер: 26, Страницы: 4226-4232 Страниц : 7 DOI: 10.1002/ejoc.201900389

Авторы

Argunov Dmitry A. ¹ , Trostianetskaia Anastasiia S. ^2,1 , Krylov Vadim B. ¹ , Kurbatova Ekaterina A. ³ , Nifantiev Nikolay E. ¹

Организации

1	Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian Federation
2	Higher Chemical College, N.D. Zelinsky Institute of Organic Chemistry, D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, 125047 Moscow, Russia
3	Laboratory of Immunology, N.D. Zelinsky Institute of Organic Chemistry, I. I. Mechnikov Research Institute for Vaccines and Sera, Moscow, Russia

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.

Argunov D.A. , Trostianetskaia A.S. , Krylov V.B. , Kurbatova E.A. , Nifantiev N.E.
Convergent Synthesis of Oligosaccharides Structurally Related to Galactan I and Galactan II of Klebsiella Pneumoniae and their Use in Screening of Antibody Specificity
European Journal of Organic Chemistry. 2019. V.2019. N26. P.4226-4232. DOI: 10.1002/ejoc.201900389 WOS Scopus OpenAlex

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