title: Twisted alpha-keto amides as transition-state analogues for acyl-transfer reactions: synthesis of the immunoconjugates.
abstract: Two new haptens were employed as antigens to elicit antibodies for acyl-transfer reactions. The haptens, both alpha-keto amides were designed to elicit antibodies which could twist potential substrates into a much more reactive conformation. The rationale for their design, synthesis, and immunization protocols will be discussed.
authors.affiliation: Department of Molecular Biology, Scripps Research Institute, La Jolla, California 92037.
authors.forename: J
authors.initials: J
authors.lastname: Yli-Kauhaluoma
authors.forename: K D
authors.initials: KD
authors.lastname: Janda
mesh_terms: D000215:Acylation; D000217:Acyltransferases; D000577:Amides / Q000737:chemistry*; D000818:Animals; D000911:Antibodies, Monoclonal; D002384:Catalysis; D004797:Enzyme-Linked Immunosorbent Assay; D005977:Glutarates / Q000737:chemistry*; D006241:Haptens; D006825:Hybridomas / Q000276:immunology; D006868:Hydrolysis; D007166:Immunosuppressive Agents / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008815:Mice, Inbred Strains / Q000276:immunology; D008968:Molecular Conformation; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000737:chemistry; D010655:Phenylenediamines / Q000737:chemistry*; D011090:Polyenes / Q000737:chemistry; D020123:Sirolimus; D013329:Structure-Activity Relationship; D016559:Tacrolimus / Q000737:chemistry; D013917:Thrombin / Q000037:antagonists & inhibitors
chemical_list: C091068:5-((4-(((4-methoxyphenyl)-oxoacetyl) methylamino)phenyl)methylamino)-5-oxopentanoic acid; C091066:5-((4-(((4-methoxyphenyl)oxoacetyl)amino)phenyl)amino)-5-oxopentanoic acid; D000577:Amides; D000911:Antibodies, Monoclonal; D005977:Glutarates; D006241:Haptens; D007166:Immunosuppressive Agents; D010456:Peptides, Cyclic; D010655:Phenylenediamines; D011090:Polyenes; C081986:cyclotheonamide A; D000217:Acyltransferases; D013917:Thrombin; D020123:Sirolimus; D016559:Tacrolimus