Catalytic antibody/substrate intermediates
AssigneeThe Scripps Research Institute
InventorsCarlos F. Barbas, III, Richard A. Lerner, Juergen Wagner
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Abstract
Antibodies that catalyze the aldol reaction are generated by immunization with a reactive compound that covalently traps a Lysine (Lys) residue in the binding pocket of the antibody by formation of a stable vinylogous amide, i.e., a covalent antibody/hapten complex. The resultant catalytic antibodies employ a catalytic mechanism which mimics the catalytic mechanism employed by natural class I aldolase enzymes.
Claims7
A process for producing a first reaction intermediate having a Schiff base, the process comprising the following step:
- condensing a first reactant with a catalyst for producing said first reaction intermediate,
- wherein
- said catalyst having a catalytic amino group, said catalyst being selected from a group consisting of catalytic antibodies and catalytic molecules containing an antibody combining site portion characterized by having a lysine with an .epsilon.-amino group;
- said first reactant having a carbonyl group;
- and
- in said condensing step, the oxygen of the carbonyl group of said first reactant is displaced by the nitrogen of the catalytic amino group of said catalyst for forming said Schiff base, said Schiff base linking said first reactant to said catalyst for producing said first reaction intermediate.
A first reaction intermediate having a Schiff base produced by condensing a first reactant with a catalyst wherein:
- said catalyst having a catalytic amino group and being selected from a group consisting of catalytic antibodies and catalytic molecules containing an antibody combining site portion characterized by having a lysine with an .epsilon.-amino group;
- said first reactant having a carbonyl group, and
- in said condensing step, the oxygen of the carbonyl group of said first reactant is displaced by the nitrogen of the catalytic amino group of said catalyst for forming said Schiff base, said Schiff base linking said first reactant to said catalyst for producing said first reaction intermediate.
An adduct produced by condensing a .beta.-dicarbonylic molecule with a catalyst having a catalytic amino group, the catalyst being selected from a group consisting of catalytic antibodies and catalytic molecules containing an antibody combining site portion characterized by having a lysine with an .epsilon.-amino group.
Dependencies are inferred from the claim text.