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Synthesis of Fluorinated Leishmania Cap Trisaccharides for Diagnostic Tool and Vaccine Development
Author(s) -
Baumann Andreas,
Marchner Stefan,
Daum Markus,
HoffmannRöder Anja
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800384
Subject(s) - chemistry , glycoconjugate , glycan , immunogenicity , hapten , leishmania , epitope , antigen , lipophosphoglycan , glycosylation , biochemistry , antigenicity , glycome , leishmania donovani , computational biology , glycoprotein , leishmaniasis , visceral leishmaniasis , immunology , biology , parasite hosting , world wide web , computer science
Bearing in mind the often insufficient metabolic stability of carbohydrate antigens, which impairs both the bioavailability and immunogenicity of a given hapten, the development of chemically modified analogs with improved antigenicity is an important step towards effective glycoconjugate vaccines. Recently, strategic glycan fluorination has become an interesting approach to this, and several examples of fluorinated carbohydrate antigens that show better metabolic stabilities and comparable or even enhanced immunogenicities have been reported to date. In this paper, we present a small library of fluorinated trisaccharides based on a privileged motif from the lipophosphoglycan capping structure of Leishmania donovani , a protozoan parasite responsible for fatal visceral leishmaniasis. These epitope analogs were synthesized by a sequential [1+1+1] glycosylation strategy. An amine linker is present at the reducing end to allow conjugation and enable future applications in immunological studies for the development of diagnostic tools and vaccines.