Transfer of stereochemical information in a minimal self-replicating system

[GRAPHICS] The rational design, synthesis, and characterization of a minimal self-repl icating system based on a 1,3-dipolar cycloaddition between a nitrone and a maleimide is presented. The importance of molecular recognition in this sy stem is demonstrated using a competitive inhibitor. Doping experiments demo nstrate that only one of the two diastereoisomeric products of the cycloadd ition reaction is capable of acting as an efficient template for its own fo rmation, accelerating the reaction between the nitrone and maleimide and co ntrolling the stereochemical outcome of the reaction.