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

González-García, Jorge; Tomić, Sanja; Lopera, Alberto; Guijarro, Lluís; Piantanida, Ivo; García-España, Enrique (2015) Aryl-bis-(scorpiand)-aza receptors differentiate between nucleotide monophosphates by a combination of aromatic, hydrogen bond and electrostatic interactions. Organic and Biomolecular Chemistry, 13 (6). pp. 1732-1740. ISSN 1477-0520

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Abstract

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.

Item Type: Article
Uncontrolled Keywords: scorpiand receptor; nucleotide recognition; NMR; fluorescence
Subjects: NATURAL SCIENCES > Physics
NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Division of Physical Chemistry
Projects:
Project titleProject leaderProject codeProject type
Dizajn, sinteza i ispitivanje interakcija malih molekula s DNA, RNA i proteinima[202026] Ivo Piantanida098-0982914-2918MZOS
Proučavanje biomakromolekula računalnim metodama i razvoj novih algoritama[113604] Sanja Tomić098-1191344-2860MZOS
Depositing User: Sanja Tomić
Date Deposited: 06 May 2015 13:27
Last Modified: 06 May 2015 13:27
URI: http://fulir.irb.hr/id/eprint/1905
DOI: 10.1039/c4ob02084g

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