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Enantiodiscrimination of Inherently Chiral Thiacalixarenes by Residual Dipolar Couplings
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SYSNO ASEP 0568178 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Enantiodiscrimination of Inherently Chiral Thiacalixarenes by Residual Dipolar Couplings Author(s) 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)Source Title Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263
Roč. 89, č. 14 (2024), s. 9711-9720Number of pages 10 s. Language eng - English Country US - United States Keywords polypeptide liquid crystals ; deuterium NMR spectroscopy ; alignment medium OECD category Organic chemistry Method of publishing Open access Institutional support UOCHB-X - RVO:61388963 UT WOS 000920494700001 EID SCOPUS 85146570802 DOI https://doi.org/10.1021/acs.joc.2c02594 Annotation 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. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2025 Electronic address https://doi.org/10.1021/acs.joc.2c02594
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