{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,7]],"date-time":"2026-07-07T14:38:31Z","timestamp":1783435111038,"version":"3.54.6"},"reference-count":54,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2025,2,28]],"date-time":"2025-02-28T00:00:00Z","timestamp":1740700800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"J\u00e1nos Bolyai Research Scholarship of the Hungarian Academy of Sciences","award":["\u00daNKP-23-5-SE-5"],"award-info":[{"award-number":["\u00daNKP-23-5-SE-5"]}]},{"name":"J\u00e1nos Bolyai Research Scholarship of the Hungarian Academy of Sciences","award":["NKFIH FK 146930"],"award-info":[{"award-number":["NKFIH FK 146930"]}]},{"name":"J\u00e1nos Bolyai Research Scholarship of the Hungarian Academy of Sciences","award":["101130235"],"award-info":[{"award-number":["101130235"]}]},{"name":"Bolyai+ New National Excellence Program of the Ministry of Human Capacities","award":["\u00daNKP-23-5-SE-5"],"award-info":[{"award-number":["\u00daNKP-23-5-SE-5"]}]},{"name":"Bolyai+ New National Excellence Program of the Ministry of Human Capacities","award":["NKFIH FK 146930"],"award-info":[{"award-number":["NKFIH FK 146930"]}]},{"name":"Bolyai+ New National Excellence Program of the Ministry of Human Capacities","award":["101130235"],"award-info":[{"award-number":["101130235"]}]},{"name":"National Research, Development and Innovation Office, Hungary","award":["\u00daNKP-23-5-SE-5"],"award-info":[{"award-number":["\u00daNKP-23-5-SE-5"]}]},{"name":"National Research, Development and Innovation Office, Hungary","award":["NKFIH FK 146930"],"award-info":[{"award-number":["NKFIH FK 146930"]}]},{"name":"National Research, Development and Innovation Office, Hungary","award":["101130235"],"award-info":[{"award-number":["101130235"]}]},{"name":"European Union\u2019s Horizon Europe research and innovation program","award":["\u00daNKP-23-5-SE-5"],"award-info":[{"award-number":["\u00daNKP-23-5-SE-5"]}]},{"name":"European Union\u2019s Horizon Europe research and innovation program","award":["NKFIH FK 146930"],"award-info":[{"award-number":["NKFIH FK 146930"]}]},{"name":"European Union\u2019s Horizon Europe research and innovation program","award":["101130235"],"award-info":[{"award-number":["101130235"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The tetrahydroisoquinoline skeleton is a pharmacologically significant core structure containing chiral centers, making enantiomeric separation crucial due to the potentially distinct biological effects of each enantiomer. In this study, laudanosine (N-methyl-tetrahydropapaverine) and its three derivatives (6\u2032-bromo-laudanosine, norlaudanosine, and N-propyl-norlaudanosine) were synthesized and used as model compounds to investigate chiral recognition mechanisms. Screening over twenty cyclodextrins (CyDs) as chiral selectors in capillary electrophoresis (CE), we found anionic CyDs to be the most effective, with sulfated-\u03b3-CyD (S-\u03b3-CyD) achieving a maximum Rs of 10.5 for laudanosine. Notably, octakis-(6-deoxy-6-(2-carboxyethyl)-thio)-\u03b3-CyD (sugammadex, SGX), heptakis-(2,3-O-diacetyl-6-O-sulfo)-\u03b2-CD (HDAS), heptakis-(2,3-O-dimethyl-6-O-sulfo)-\u03b2-CD (HDMS), and octakis-(2,3-O-dimethyl-6-O-sulfo)-\u03b3-CD (ODMS) provided excellent enantioseparation for all four analytes. Following HPLC screening on CyD-based and polysaccharide-based chiral stationary phases, semi-preparative HPLC methods using amylose and cellulose-based columns were optimized to isolate enantiomers. The purity of the isolated enantiomers was evaluated by HPLC, and their configurations were confirmed via circular dichroism spectroscopy. The isolated enantiomers allowed us to explore enantiomer migration order reversals in CE and enantiomer elution order reversal in HPLC. Further 1H and 2D ROESY NMR experiments provided atomic-level insights into enantioselective complex formation, confirming enantiomer differentiation by SGX and elucidating the inclusion complex structure, where the ring C immersion into the CyD cavity is prevalent.<\/jats:p>","DOI":"10.3390\/molecules30051125","type":"journal-article","created":{"date-parts":[[2025,2,28]],"date-time":"2025-02-28T10:12:33Z","timestamp":1740737553000},"page":"1125","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Chiral Recognition Mechanism of Benzyltetrahydroisoquinoline Alkaloids: Cyclodextrin-Mediated Capillary Electrophoresis, Chiral HPLC, and NMR Spectroscopy Study"],"prefix":"10.3390","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0009-0004-8348-4545","authenticated-orcid":false,"given":"Erzs\u00e9bet","family":"V\u00e1rnagy","sequence":"first","affiliation":[{"name":"Department of Pharmacognosy, Semmelweis University, \u00dcll\u0151i \u00fat 26, H-1085 Budapest, Hungary"},{"name":"Center for Pharmacology and Drug Research & Development, Semmelweis University, \u00dcll\u0151i \u00fat 26, H-1085 Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5341-319X","authenticated-orcid":false,"given":"Gerg\u0151","family":"T\u00f3th","sequence":"additional","affiliation":[{"name":"Center for Pharmacology and Drug Research & Development, Semmelweis University, \u00dcll\u0151i \u00fat 26, H-1085 Budapest, Hungary"},{"name":"Department of Pharmaceutical Chemistry, Semmelweis University, H\u0151gyes Endre utca 9, H-1092 Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"S\u00e1ndor","family":"Hosztafi","sequence":"additional","affiliation":[{"name":"Center for Pharmacology and Drug Research & Development, Semmelweis University, \u00dcll\u0151i \u00fat 26, H-1085 Budapest, Hungary"},{"name":"Department of Pharmaceutical Chemistry, Semmelweis University, H\u0151gyes Endre utca 9, H-1092 Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"M\u00e1t\u00e9","family":"Dob\u00f3","sequence":"additional","affiliation":[{"name":"Center for Pharmacology and Drug Research & Development, Semmelweis University, \u00dcll\u0151i \u00fat 26, H-1085 Budapest, Hungary"},{"name":"Department of Pharmaceutical Chemistry, Semmelweis University, H\u0151gyes Endre utca 9, H-1092 Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ida","family":"Fej\u0151s","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, Semmelweis University, \u00dcll\u0151i \u00fat 26, H-1085 Budapest, Hungary"},{"name":"Center for Pharmacology and Drug Research & Development, Semmelweis University, \u00dcll\u0151i \u00fat 26, H-1085 Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7056-6825","authenticated-orcid":false,"given":"Szabolcs","family":"B\u00e9ni","sequence":"additional","affiliation":[{"name":"Integrative Health and Environmental Analysis Research Laboratory, Department of Analytical Chemistry, Institute of Chemistry, ELTE E\u00f6tv\u00f6s Lor\u00e1nd University, P\u00e1zm\u00e1ny P\u00e9ter s\u00e9t\u00e1ny 1\/A, H-1117 Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,2,28]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Powder-George, Y.L. 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