Scripps Clinic and Research Foundation

Alfonso Tramontano

Richard A Lerner

Andrew D Napper

Kim D Janda

A method of separating a pair of stereoisomers, and especially enantiomers, using monoclonal receptor molecules containing an antibody combining site that binds to substantially only one of that pair of stereoisomers is disclosed.

Stereoisomer separation method using antibody combing site-containing

A phosphorus-containing analog-ligand having a stereoconfiguration that substantially corresponds to the stereoconfiguration of an amide- or ester-forming transition state is used to induce production of receptor molecules whose antibody combining sites have stereospecific amide or ester synthase catalytic activity when reacted with a ligand containing (i) a carbonyl carbon atom and (ii) an amine or alcohol group that are structurally capable of forming a preselected stereoisomer of a carboxylic amide or ester.

Antibody combining sites that exhibit stereoselective synthase activity,

An analog-ligand having a conformation that substantially corresponds to the conformation of a hydrolytic transition state of an amide or ester reactant ligand is used to produce receptor molecules of predetermined specificity. The receptor molecules include an antibody combining site that binds to a reactant ligand and thereby stabilizes the tetrahedral carbon atom of the amide or ester hydrolysis transition state of that reactant ligand to catalytically hydrolyze the reactant ligand at a predetermined site.

Antibodies which catalyze hydrolysis of ester bonds

A phosphorous-containing analog-ligand having a conformation that substantially corresponds to the conformation of an amide- or ester-forming transition state is used to induce production of receptor molecules whose antibody combining sites have amide or ester synthase catalytic activity when reacted with a ligand containing (i) a carbonyl carbon atom and (ii) an amine or alcohol group that are structurally capable of forming a preselected carboxylic amide or ester bond.

Antibody combining sites that exhibit amide or ester synthase activity

A phosphonamidate or phosphonate analog-ligand having a conformation that substantially corresponds to the conformation of a hydrolytic transition state of an amide or ester ligand is used to produce antibodies of predetermined specificity. The antibodies include an epitope that binds to and thereby stabilizes the tetrahedral carbon atom of the amide or ester hydrolysis transition state of the ligand to hydrolyze the ligand at a predetermined site.

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San Diego, CA, United States of America

Alfonso Tramontano