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Zwitterionic Phosphorylated Quinines as Chiral Solvating Agents for NMR Spectroscopy
Author(s) -
RudzińskaSzostak Ewa,
Górecki Łukasz,
Berlicki Łukasz,
Ślepokura Katarzyna,
Mucha Artur
Publication year - 2015
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22494
Subject(s) - chemistry , moiety , enantiomer , chirality (physics) , nuclear magnetic resonance spectroscopy , enantioselective synthesis , phosphate , chiral derivatizing agent , hydrogen bond , organic chemistry , salt (chemistry) , proton nmr , combinatorial chemistry , molecule , stereochemistry , catalysis , chiral column chromatography , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
Because of their unique 3D arrangement, naturally occurring Cinchona alkaloids and their synthetic derivatives have found wide‐ranging applications in chiral recognition . Recently, we determined the enantioselective properties of C‐9‐phosphate mixed triesters of quinine as versatile chiral solvating agents in nuclear magnetic resonance (NMR) spectroscopy. In the current study, we introduce new zwitterionic members of this class of molecules containing a negatively charged phosphate moiety (i.e., ethyl, n ‐butyl and phenyl hydrogen quininyl phosphate). An efficient approach for synthesizing these compounds is elaborated, and full characterization, including conformational and autoaggregation phenomena studies, was performed. Therefore, their ability to induce NMR anisochrony of selected enantiomeric substrates (i.e., primarily N ‐DNB‐protected amino acids and their methyl esters) was analyzed compared to uncharged diphenyl quininyl phosphate and its positively charged quaternary ammonium hydrochloride salt. In addition, 1 H and 13 C NMR experiments revealed their enantiodiscrimination potential toward novel analytes, such as secondary amines and nonprotected amino acids . Chirality 27:752–760, 2015 . © 2015 Wiley Periodicals, Inc.