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Concise and modular synthesis of regioisomeric haptens for the production of high-affinity and stereoselective antibodies to the strobilurin azoxystrobin

AuthorsParra, Javier ; Mercader Badia, Josep Vicent ; Agulló, Consuelo; Abad Fuentes, Antonio ; Abad Somovilla, Antonio
KeywordsHapten design
Linker attachment site
Molecular recognition
C−C coupling
Issue Date2011
CitationTetrahedron 67: 624- 635 (2011)
AbstractThe 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.
Identifiersdoi: 10.1016/j.tet.2010.11.054
issn: 0040-4020
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