6533b827fe1ef96bd1286fbd
RESEARCH PRODUCT
Aryl-bis-(scorpiand)-aza receptors differentiate between nucleotide monophosphates by a combination of aromatic, hydrogen bond and electrostatic interactions.
Lluis GuijarroEnrique García-españaSanja TomićJorge González-garcíaIvo PiantanidaAlberto Loperasubject
Models MolecularMacrocyclic CompoundsMagnetic Resonance Spectroscopyscorpiand receptor; nucleotide recognition; NMR; fluorescenceStereochemistryStatic ElectricityStackingProtonation010402 general chemistry01 natural sciencesBiochemistryPhosphateschemistry.chemical_compoundMoietyNucleotidePhysical and Theoretical Chemistrychemistry.chemical_classificationAza CompoundsMolecular Structure010405 organic chemistryHydrogen bondChemistryNucleotidesPhysicsArylBiomoleculeOrganic ChemistryHydrogen BondingHydrogen-Ion Concentration0104 chemical sciencesChemistrySelectivitydescription
Bis-polyaza pyridinophane scorpiands bind nucleotides in aqueous medium with 10–100 micromolar affinity, predominantly 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 with 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 with respect to other NMPs, based on the protonation of adenine heterocyclic N1. The results stress that 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-12-06 | Organicbiomolecular chemistry |