Concise and modular synthesis of regioisomeric haptens for the production of high-affinity and stereoselective antibodies to the strobilurin azoxystrobin |
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Authors: | Javier ParraJosep V. Mercader,Consuelo Agulló Antonio Abad-Fuentes,Antonio Abad-Somovilla |
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Affiliation: | a Department of Biotechnology, IATA-CSIC, Agustí Escardino 7, 46980 Paterna, València, Spain b Department of Organic Chemistry, Universitat de València, Doctor Moliner 50, 46100 Burjassot, València, Spain |
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Abstract: | The immune response to regioisomeric haptens of azoxystrobin with varied derivatization sites was studied. Based on the Sonogashira and Suzuki-Miyaura couplings and following a straightforward modular design, we have synthesized four haptens with the same linker anchored through C-C bonds and located at different sites of the molecule. The most stereoselective antibodies were produced from immunogens with the spacer arm at a distal position from the β-methoxyacrylate moiety characteristic of strobilurins. Moreover, we observed that assay cross-reactivity was reliant on the functionalization site of the competitor derivative. Finally, the antibody binding site was explored using synthetic chemical analogues. |
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Keywords: | Hapten design C-C coupling Linker attachment site Landsteiner Molecular recognition Immunochemistry |
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