title: Design and syntheses of three haptens to generate catalytic antibodies that cleave amide bonds with nucleophilic catalysis.
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.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, Cambridge 02139, USA.
authors.forename: O
authors.initials: O
authors.lastname: Ersoy
authors.forename: R
authors.initials: R
authors.lastname: Fleck
authors.forename: M J
authors.initials: MJ
authors.lastname: Blanco
authors.forename: S
authors.initials: S
authors.lastname: Masamune
mesh_terms: D000577:Amides / Q000737:chemistry; D017151:Antibodies, Catalytic / Q000737:chemistry*; D002384:Catalysis; D006241:Haptens / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D013053:Spectrophotometry
chemical_list: D000577:Amides; D017151:Antibodies, Catalytic; D006241:Haptens