CATALYTIC ANTIBODIES IN SYNTHESIS - DESIGN AND SYNTHESIS OF A HAPTEN FOR APPLICATION TO THE PREPARATION OF A SCALEMIC PYRROLIDINE RING SYNTHON FOR PTILOMYCALIN-A

A catalytic antibody-based approach toward the synthesis of an optical ly active pyrrolidine ring synthon potentially useful for ptilomycalin A is described. Enantiomerically pure hapten 37 was designed and cons tructed with the eventual goal of generating antibodies for the enanti oselective partial hydrolysis of a meso diester such as 44 into a mono acid 45. This transition state analog possesses a phosphonate group co ntaining the requisite oxyanionic character of the tetrahedral interme diate for ester hydrolysis. A newly developed carbamate-based linker, which was found to be much more hydrolytically stable than the commonl y used glutarate ester, was developed for coupling of the hapten to a carrier protein.