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Synthesis and Antibody Binding of Highly Fluorinated Amphiphilic MUC1 Glycopeptide Antigens
Author(s) -
Platen Tobias,
Schüler Timo,
Tremel Wolfgang,
HoffmannRöder Anja
Publication year - 2011
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.201100648
Subject(s) - chemistry , epitope , muc1 , glycan , glycopeptide , antigen , antibody , combinatorial chemistry , biochemistry , glycoprotein , immunology , mucin , biology , antibiotics
The analysis of humoral immune responses is of great importance for basic and clinical research. Mapping the structural requirements of epitope recognition with modified tumor‐associated carbohydrate antigens allows both the development of biomarkers and the design of synthetic anticancer vaccines. For this purpose, double‐tailed hydrocarbon/fluorocarbon membrane anchors have been prepared and conjugated to a T N dipeptide. Furthermore, a novel hydrophobized MUC1 tandem repeat glycopeptide antigen was fully assembled on a solid support and its specific binding to different mouse anti‐MUC1 antibodies was demonstrated through ELISA, QCM, and SPR measurements. Such functional fluorous MUC1 antigens are of great interest for specific glycan (micro‐)array formats and allow a detailed analyses of serum antibodies obtained from immunization studies. In addition, the intriguing characteristics of fluorous surfactants, for example, their strong self‐association tendency, might stimulate the use of novel fluorous‐tagged antigen conjugates in the development of multivalent micellar glycopeptide vaccines.