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Synthesis and Immunochemical characterization of S ‐linked Glycoconjugate Vaccines against Candida albicans
Author(s) -
Wu Xiangyang,
Lipinski Tomasz,
Paszkiewicz Eugenia,
Bundle David R.
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200800352
Subject(s) - glycoconjugate , trisaccharide , chemistry , epitope , bovine serum albumin , glycosidic bond , biochemistry , mannan , residue (chemistry) , candida albicans , toxoid , stereochemistry , antigen , microbiology and biotechnology , biology , enzyme , immunization , polysaccharide , genetics
Replacement of the glycosidic oxygen atom by a sulphur atom is a promising technique for creating glycoconjugates with increased resistance to hydrolysis by endogenous glycosidases. The synthesis and antigenic properties of two distinct (1→2)‐β‐mannan trisaccharides with inter residue‐ S ‐linked mannopyranose residues are described. Syntheses were based on an oxidation–reduction strategy to construct the O ‐linked β‐mannopyranoside bonds and a S N 2 inversion to provide 1‐thio‐β‐mannopyranoside residues. Subsequently the allyl trisaccharide glycosides were subjected to photo addition with cysteine amine and coupled to tetanus toxoid and bovine serum albumin with good efficiency via an adipic acid tether. Rabbit immunization studies revealed that the antibodies elicited by the two glycoconjugates were able to recognize the corresponding O ‐linked trisaccharide epitope conjugated to BSA and the native cell wall antigen of Candida albicans .