Anion-Sensing Properties of Cyclopentaphenylalanine

Petters, Ivan; Modrušan, Matija; Vidović, Nikolina; Crnolatac, Ivo; Cindro, Nikola; Piantanida, Ivo; Speranza, Giovanna; Horvat, Gordan; Tomišić, Vladislav (2022) Anion-Sensing Properties of Cyclopentaphenylalanine. Molecules, 27 (12). ISSN 1420-3049

PDF - Published Version - article Available under License Creative Commons Attribution. Download (4MB)

Abstract

Cyclic pentaphenylalanine was studied as an efficient anion sensor for halides, thiocyanate and oxoanions in acetonitrile and methanol. Stability constants of the corresponding complexes were determined by means of fluorimetric, spectrophotometric, 1H NMR, and microcalorimetric titrations. A detailed structural overview of receptor–anion complexes was obtained by classical molecular dynamics (MD) simulations. The results of 1H NMR and MD studies indicated that the bound anions were coordinated by the amide groups of cyclopeptide, as expected. Circular dichroism (CD) titrations were also carried out in acetonitrile. To the best of our knowledge, this is the first example of the detection of anion binding by cyclopeptide using CD spectroscopy. The CD spectra were calculated from the structures obtained by MD simulations and were qualitatively in agreement with the experimental data. The stoichiometry of almost all complexes was 1:1 (receptor:anion), except for dihydrogen phosphate where the binding of dihydrogen phosphate dimer was observed in acetonitrile. The affinity of the cyclopeptide receptor was correlated with the structure of anion coordination sphere, as well as with the solvation properties of the examined solvents.

Item Type:	Article
Uncontrolled Keywords:	cyclopeptide; anion binding; fluorimetry; circular dichroism; UV spectrometry; 1H NMR; MD simulations; solvent effect
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry
Projects:	Project title Project leader Project code Project type Koordinacijske reakcije makrocikličkih liganada u otopini-MacroSol Vladislav Tomišić IP-2019-04-9560 HRZZ Višekromoforne probe za prepoznavanje pojedinih struktura DNA, RNA i proteina-BioMultiChromoProbes Ivo Piantanida IP-2018-01-5475 HRZZ
Depositing User:	Diana Mikoč Radešić
Date Deposited:	31 Jan 2024 10:07
URI:	http://fulir.irb.hr/id/eprint/8427
DOI:	10.3390/molecules27123918

Actions (login required)

View Item