Synthesis and Preliminary Immunological Evaluation of a Pseudotetrasaccharide Related to a Repeating Unit of the Streptococcus pneumoniae Serotype 6A Capsular Polysaccharide

Synthesis and Preliminary Immunological Evaluation of a Pseudotetrasaccharide Related to a Repeating Unit of the Streptococcus pneumoniae Serotype 6A Capsular Polysaccharide Full article

Journal

Frontiers in Molecular Biosciences
ISSN: 2296-889X

Output data

Year: 2021, Volume: 8, Article number : 754753, Pages count : DOI: 10.3389/fmolb.2021.754753

Authors

Sukhova Elena V. ¹ , Yashunsky Dmitry V. ¹ , Kurbatova Ekaterina A. ² , Akhmatova Elina A. ² , Tsvetkov Yury E. ¹ , Nifantiev Nikolay E. ¹

Affiliations

1	Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
2	Laboratory of Therapeutic Vaccines, Mechnikov Research Institute for Vaccines and Sera, Moscow, Russia

2-Aminoethyl glycoside of the pseudotetrasaccharide α-d-Glcp-(1→3)-α-l-Rhap-(1→3)-d-Rib-ol-(5-P-2)-α-d-Galp corresponding to a repeating unit of the Streptococcus pneumoniae type 6A capsular polysaccharide has been synthesized. A suitably protected pseudotrisaccharide α-d-Glcp-(1→3)-α-l-Rhap-(1→3)-d-Rib-ol with a free 5-OH group in the ribitol moiety and a 2-OH derivative of 2-trifluoroacetamidoethyl α-d-galactopyranoside have been efficiently prepared and then connected via a phosphate bridge using the hydrogen phosphonate procedure. Preliminary immunological evaluation of this pseudotetrasaccharide and the previously synthesized pseudotetrasaccharide corresponding to a repeating unit of the capsular polysaccharide of S. pneumoniae serotype 6B has shown that they contain epitopes specifically recognized by anti-serogroup 6 antibodies and are able to model well the corresponding capsular polysaccharides. Conjugates of the synthetic pseudotetrasaccharides with bovine serum albumin were shown to be immunogenic in mice.

Sukhova E.V. , Yashunsky D.V. , Kurbatova E.A. , Akhmatova E.A. , Tsvetkov Y.E. , Nifantiev N.E.
Synthesis and Preliminary Immunological Evaluation of a Pseudotetrasaccharide Related to a Repeating Unit of the Streptococcus pneumoniae Serotype 6A Capsular Polysaccharide
Frontiers in Molecular Biosciences. 2021. V.8. 754753 . DOI: 10.3389/fmolb.2021.754753 WOS Scopus OpenAlex

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