Zwitterionic Phosphorylated Quinines as Chiral Solvating Agents for NMR Spectroscopy. Issue 10 (25th August 2015)

• Record Type: Journal Article
• Authors: Rudzińska‐Szostak, Ewa; Górecki, Łukasz; Berlicki, Łukasz; Ślepokura, Katarzyna; Mucha, Artur
• Is Part Of: Chirality. Volume 27:Issue 10(2015)
• Page Start: 752
• Page End: 760
• Publication Date: 2015-08-25
• Subjects: Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.22494
• Languages: English
• ISSNs: 0899-0042

Abstract

<abstract abstract-type="main"> <title>Abstract</title> <p>Because of their unique 3D arrangement, naturally occurring <italic>Cinchona</italic> alkaloids and their <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">synthetic derivatives</named-content> have found wide‐ranging applications in <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">chiral recognition</named-content>. Recently, we determined the <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">enantioselective</named-content> properties of C‐9‐phosphate mixed triesters of quinine as versatile chiral solvating agents in <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">nuclear magnetic resonance</named-content> (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, <italic>n</italic>‐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 <italic>N</italic>‐DNB‐protected <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">amino acids</named-content> and their methyl esters) was analyzed compared to uncharged diphenyl quininyl phosphate and its positively charged quaternary ammonium hydrochloride salt. In addition, <sup>1</sup>H and <sup>13</sup>C NMR experiments revealed their enantiodiscrimination potential toward novel analytes, such as secondary amines and nonprotected <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">amino acids</named-content>. <italic>Chirality 27:752–760, 2015</italic>. © 2015 Wiley Periodicals, Inc.</p> </abstract>