Aryl-bis-(scorpiand)-aza receptors differentiate between nucleotide monophosphates by combination of aromatic, hydrogen bond and electrostatic interactions (CROSBI ID 212656)
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González-García, Jorge ; Tomić, Sanja ; Lopera, Alberto ; Guijarro, Lluís ; Piantanida, Ivo ; García-España, Enrique
engleski
Aryl-bis-(scorpiand)-aza receptors differentiate between nucleotide monophosphates by combination of aromatic, hydrogen bond and electrostatic interactions
Bis-polyaza pyridinophane scorpiands bind nucleotides in aqueous medium by 10-100 micromolar affinity, dominantly by electrostatic interactions between nucleotide phosphates and protonated aliphatic amines and assisted by aromatic stacking interactions. The pyridine-scorpiand receptor showed rare selectivity toward CMP in respect to other nucleotides, whereby two orders of magnitude affinity difference between CMP and UMP was the most appealing. The phenanthroline-scorpiand receptor revealed at pH 5 strong selectivity toward AMP in respect to other NMPs, based on the protonation of adenine heterocyclic N1. Results stress the efficient recognition of small biomolecules within scorpiand-like receptors relies mostly on the electrostatic and H-bonding interactions despite the competitive interactions in the bulk solvent, thus supporting further optimisation of this versatile artificial moiety.
scorpiand receptor; nucleotide recognition; NMR; fluorescence
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