Acceleration of a Phosphate Diester Transesterification Reaction by Bis(alkylguanidinium) Receptors Containing an Appended General Base

Abstract

Rate enhancements up to 290-fold are possible for the transesterification of 2-hydroxypropyl-p-nitrophenylphosphate when bis(guanidinium) catalysts bearing basic groups are added. The combination of the appended base and the electrostatic complementarity of substrate and receptor (see complex 1) make the guanidinium compounds efficient enzyme mimics. These types of compounds may have therapeutic applications as artificial nucleases.