172885-54-0Relevant articles and documents
Catalytic antibodies in synthesis: Design and synthesis of a hapten for application to the preparation of a scalemic pyrrolidine ring synthon for ptilomycalin A
Anderson, Glen T.,Alexander, Michael D.,Taylor, Scott D.,Smithrud, David B.,Benkovic, Stephen J.,Weinreb, Steven M.
, p. 125 - 132 (2007/10/03)
A catalytic antibody-based approach toward the synthesis of an optically active pyrrolidine ring synthon potentially useful for ptilomycalin A is described. Enantiomerically pure hapten 37 was designed and constructed with the eventual goal of generating antibodies for the enantioselective partial hydrolysis of a mesoo diester such as 44 into a monoacid 45. This transition state analog possesses a phosphonate group containing the requisite oxyanionic character of the tetrahedral intermediate for ester hydrolysis. A newly developed carbamate-based linker, which was found to be much more hydrolytically stable than the commonly used glutarate ester, was developed for coupling of the hapten to a carrier protein.
