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Synthesis of a Dimeric Lewis Antigen and the Evaluation of the Epitope Specificity of Antibodies Elicited in Mice

✍ Scribed by Therese Buskas; Yanhong Li; Geert-Jan Boons

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
207 KB
Volume
11
Category
Article
ISSN
0947-6539

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✦ Synopsis

Abstract

The Lewis^y^–Lewis^x^ heptasaccharide, modified by an artificial aminopropyl spacer, was synthesized by an approach that employed two orthogonally protected lactosamine building blocks. A p‐(benzoyl)‐benzyl glycoside was used as a novel anomeric protecting group, which could be selectively removed at a late stage in the synthesis, thus offering the benefit of enhanced flexibility. The artificial aminopropyl moiety was modified by a thioacetyl group, which allowed an efficient conjugation to keyhole limpet hemocyanin (KLH) that had been activated with electrophilic 3‐(bromoacetamido)‐propionyl groups. Mice were immunized with the Le^y^Le^x^–BrAc–KLH antigen. Analysis of the sera by ELISA established that a strong helper T‐cell immune response was raised against the Le^y^Le^x^ saccharide. Further ELISA analysis showed that the titer for monomeric Le^y^ tetrasaccharide was tenfold lower whereas recognition of the Le^x^ trisaccharide was negligible.

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