6533b7d9fe1ef96bd126ccf3
RESEARCH PRODUCT
Concise and modular synthesis of regioisomeric haptens for the production of high-affinity and stereoselective antibodies to the strobilurin azoxystrobin
Josep V. MercaderJ.l. ParraAntonio Abad-fuentesAntonio Abad-somovillaConsuelo Agullósubject
Hapten designStereochemistryChemistryImmunochemistryOrganic ChemistryC−C couplingSonogashira couplingLandsteinerBiochemistryChemical synthesisStrobilurinschemistry.chemical_compoundMolecular recognitionLinker attachment siteDrug DiscoveryMoietyMolecular recognitionDerivatizationLinkerHaptendescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2011-01-01 | Tetrahedron |