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

Dmitry V. Yashunsky¹  Elena V. Sukhova¹  Nikolay E. Nifantiev¹  Yury E. Tsvetkov¹  Elina A. Akhmatova²  Ekaterina A. Kurbatova² 

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

关键词: Streptococcus pneumoniae serotype 6A;    capsular polysaccharide;    conjugate vaccines;    repeating unit;    phosphodiester;    synthesis;   

DOI  :  10.3389/fmolb.2021.754753

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown