Polyhydroxylated Sapphyrins: Multisite Non-metallic Catalysts for Activated Phosphodiester Hydrolysis

Enhanced hydrolysis rates for the cleavage of bis(4-nitrophenyl)phosphate (BNPP), a model
phosphodiester, may be achieved by using appropriately designed ditopic receptors containing the known
phosphate-binding nucleus, sapphyrin, attached covalently to suitably oriented polyhydroxyl subunits.
Evidence for the interaction between sapphyrin and BNPP comes from solid-state X-ray diffraction analysis
of a diprotonated dihydroxylated sapphyrin−BNPP complex and from solution-phase 31P NMR spectroscopic
binding studies. The sapphyrins described in this paper may have a role to play as oligonucleotide cleavage
agents.