Статья

Catalytic Sulfation of Betulin with Sulfamic Acid: Experiment and DFT Calculation

Аleksandr S. KazachenkoDepartment of Organic and Analytical Chemistry, Institute of Nonferrous Metals and Materials Science, Siberian Federal University, pr. Svobodny 79, 660041 Krasnoyarsk, RussiaFeride AkmanVocational School of Food, Agriculture and Livestock, University of Bingöl, Bingöl 12000, TurkeyNatalya VasilievaDepartment of Organic and Analytical Chemistry, Institute of Nonferrous Metals and Materials Science, Siberian Federal University, pr. Svobodny 79, 660041 Krasnoyarsk, RussiaNoureddine IssaouiLaboratory of Quantum and Statistical Physics (LR18ES18), Faculty of Sciences, University of Monastir, Monastir 5079, TunisiaYuriy N. MalyarDepartment of Organic and Analytical Chemistry, Institute of Nonferrous Metals and Materials Science, Siberian Federal University, pr. Svobodny 79, 660041 Krasnoyarsk, RussiaAlexandеr A. KondrasenkoInstitute of Chemistry and Chemical Technology, Krasnoyarsk Scientific Center, Siberian Branch, Russian Academy of Sciences, Akademgorodok, 50, bld. 24, 660036 Krasnoyarsk, RussiaValentina S. BorovkovaDepartment of Organic and Analytical Chemistry, Institute of Nonferrous Metals and Materials Science, Siberian Federal University, pr. Svobodny 79, 660041 Krasnoyarsk, RussiaAngelina V. MiroshnikovaDepartment of Organic and Analytical Chemistry, Institute of Nonferrous Metals and Materials Science, Siberian Federal University, pr. Svobodny 79, 660041 Krasnoyarsk, RussiaAnna S. KazachenkoDepartment of Organic and Analytical Chemistry, Institute of Nonferrous Metals and Materials Science, Siberian Federal University, pr. Svobodny 79, 660041 Krasnoyarsk, RussiaOmar M. Al-DossaryDepartment of Physics and Astronomy, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaMarek J. WójcikFaculty of Chemistry, Jagiellonian University, 30-387 Krakow, PolandYaroslava D. BerezhnayaInstitute of Chemical Technologies, Siberian State University of Science and Technology, pr. Mira 82, 660049 Krasnoyarsk, RussiaEvgeniy V. Elsuf’evInstitute of Chemistry and Chemical Technology, Krasnoyarsk Scientific Center, Siberian Branch, Russian Academy of Sciences, Akademgorodok, 50, bld. 24, 660036 Krasnoyarsk, Russia

2022en

ABI

Аннотация

Betulin is an important triterpenoid substance isolated from birch bark, which, together with its sulfates, exhibits important bioactive properties. We report on a newly developed method of betulin sulfation with sulfamic acid in pyridine in the presence of an Amberlyst®15 solid acid catalyst. It has been shown that this catalyst remains stable when being repeatedly (up to four cycles) used and ensures obtaining of sulfated betulin with a sulfur content of ~10%. The introduction of the sulfate group into the betulin molecule has been proven by Fourier-transform infrared, ultraviolet-visible, and nuclear magnetic resonance spectroscopy. The Fourier-transform infrared (FTIR) spectra contain absorption bands at 1249 and 835–841 cm−1; in the UV spectra, the peak intensity decreases; and, in the nuclear magnetic resonance (NMR) spectra, of betulin disulfate, carbons С3 and С28 are completely shifted to the weak-field region (to 88.21 and 67.32 ppm, respectively) with respect to betulin. Using the potentiometric titration method, the product of acidity constants K1 and K2 of a solution of the betulin disulfate H+ form has been found to be 3.86 × 10–6 ± 0.004. It has been demonstrated by the thermal analysis that betulin and the betulin disulfate sodium salt are stable at temperatures of up to 240 and 220 °C, respectively. The density functional theory method has been used to obtain data on the most stable conformations, molecular electrostatic potential, frontier molecular orbitals, and mulliken atomic charges of betulin and betulin disulfate and to calculate the spectral characteristics of initial and sulfated betulin, which agree well with the experimental data.

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Идентификаторы

DOI: 10.3390/ijms23031602

Цитирования и источники

Цитирований: 2Использованных источников: 0

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