Design and syntheses of three haptens to generate catalytic antibodies that cleave amide bonds with nucleophilic catalysis |
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Authors: | Ersoy O Fleck R Blanco M J Masamune S |
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Affiliation: | Department of Chemistry, Massachusetts Institute of Technology, Cambridge 02139, USA. |
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Abstract: | Design principles and syntheses of three haptens that were recently reported to generate amide bond cleaving catalytic antibodies are described. The hapten designs sought to induce acidic and/or basic residues in antibody binding sites via charge complementarity, and also to generate a hydrophobic binding pocket for an external phenol nucleophile. The charged yet aromatic nature of these haptens presented some unique synthetic challenges and solutions to which are described below. |
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