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Article

Anion-Sensing Properties of Cyclopentaphenylalanine

1
Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, 10000 Zagreb, Croatia
2
Dipartimento di Chimica, Università degli Studi di Milano, Via C. Golgi, 19, 20133 Milan, Italy
3
Institute of Agriculture and Tourism, Department of Agriculture and Nutrition, Karla Huguesa 8, 52440 Poreč, Croatia
4
Ruđer Bošković Institute, Bijenička 54, 10000 Zagreb, Croatia
*
Authors to whom correspondence should be addressed.
Academic Editor: Takahiro Kusukawa
Molecules 2022, 27(12), 3918; https://doi.org/10.3390/molecules27123918
Received: 2 June 2022 / Revised: 15 June 2022 / Accepted: 16 June 2022 / Published: 18 June 2022
(This article belongs to the Special Issue Recent Advances in Molecular Sensors)
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. View Full-Text
Keywords: cyclopeptide; anion binding; fluorimetry; circular dichroism; UV spectrometry; 1H NMR; MD simulations; solvent effect cyclopeptide; anion binding; fluorimetry; circular dichroism; UV spectrometry; 1H NMR; MD simulations; solvent effect
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MDPI and ACS Style

Petters, I.; Modrušan, M.; Vidović, N.; Crnolatac, I.; Cindro, N.; Piantanida, I.; Speranza, G.; Horvat, G.; Tomišić, V. Anion-Sensing Properties of Cyclopentaphenylalanine. Molecules 2022, 27, 3918. https://doi.org/10.3390/molecules27123918

AMA Style

Petters I, Modrušan M, Vidović N, Crnolatac I, Cindro N, Piantanida I, Speranza G, Horvat G, Tomišić V. Anion-Sensing Properties of Cyclopentaphenylalanine. Molecules. 2022; 27(12):3918. https://doi.org/10.3390/molecules27123918

Chicago/Turabian Style

Petters, Ivan, Matija Modrušan, Nikolina Vidović, Ivo Crnolatac, Nikola Cindro, Ivo Piantanida, Giovanna Speranza, Gordan Horvat, and Vladislav Tomišić. 2022. "Anion-Sensing Properties of Cyclopentaphenylalanine" Molecules 27, no. 12: 3918. https://doi.org/10.3390/molecules27123918

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