Naslov
Aryl-bis-(scorpiand)-aza receptors differentiate between nucleotide monophosphates by combination of aromatic, hydrogen bond and electrostatic interactions

Autori
González-García, Jorge ; Tomić, Sanja ; Lopera, Alberto ; Guijarro, Lluís ; Piantanida, Ivo ; García-España, Enrique

Izvornik
Organic & biomolecular chemistry (1477-0520) 13 (2015); 1732-1740

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
scorpiand receptor; nucleotide recognition; NMR; fluorescence

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Fizika, Kemija

POVEZANOST RADA