Počet záznamů: 1
Enantiodiscrimination of Inherently Chiral Thiacalixarenes by Residual Dipolar Couplings
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SYSNO ASEP 0568178 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Ostatní články Název Enantiodiscrimination of Inherently Chiral Thiacalixarenes by Residual Dipolar Couplings Tvůrce(i) Tichotová, Markéta (UOCHB-X) ORCID
Landovský, T. (CZ)
Lang, J. (CZ)
Jeziorowski, S. (DE)
Schmidts, V. (DE)
Kohout, M. (CZ)
Babor, M. (CZ)
Lhoták, P. (CZ)
Thiele, C. M. (DE)
Dvořáková, H. (CZ)Zdroj.dok. Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263
(2023)Poč.str. 10 s. Jazyk dok. eng - angličtina Země vyd. US - Spojené státy americké Klíč. slova polypeptide liquid crystals ; deuterium NMR spectroscopy ; alignment medium Obor OECD Organic chemistry Způsob publikování Open access Institucionální podpora UOCHB-X - RVO:61388963 DOI 10.1021/acs.joc.2c02594 Anotace Inherently chiral compounds, such as calixarenes, are chiral due to a nonplanar three-dimensional (3D) structure. Determining their conformation is essential to understand their properties, with nuclear magnetic resonance (NMR) spectroscopy being one applicable method. Using alignment media to measure residual dipolar couplings (RDCs) to obtain structural information is advantageous when classical NMR parameters like the nuclear Overhauser effect (NOE) or J-couplings fail. Besides providing more accurate structural information, the alignment media can induce different orientations of enantiomers. In this study, we examined the ability of polyglutamates with different side-chain moieties─poly-γ-benzyl-l-glutamate (PBLG) and poly-γ-p-biphenylmethyl-l-glutamate (PBPMLG) ─to enantiodifferentiate the inherently chiral phenoxathiin-based thiacalix[4]arenes. Both media, in combination with two solvents, allowed for enantiodiscrimination, which was, to the best of our knowledge, proved for the first time on inherently chiral compounds. Moreover, using the experimental RDCs, we investigated the calix[4]arenes conformational preferences in solution, quantitatively analyzed the differences in the alignment of the enantiomers, and discussed the pitfalls of the use of the RDC analysis. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Rok sběru 2025 Elektronická adresa https://doi.org/10.1021/acs.joc.2c02594
Počet záznamů: 1