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Enantioselective Synthesis, Enantiomeric Separations and Chiral Recognition

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Enantioselective Synthesis, Enantiomeric Separations and Chiral Recognition Maria Elizabeth Tiritan, and Carla Madalena Pinto Sofia Fernandes Garcia Enantioselective Enantiomeric Synthesis, Separations Chiral and Recognition Enantioselective Synthesis, Enantiomeric Separations and Chiral Recognition Edited by Maria Elizabeth Tiritan, Madalena Pinto and Carla Sofia Garcia Fernandes Printed Edition of the Special Issue Published in Molecules www.mdpi.com/journal/molecules Enantioselective Synthesis, Enantiomeric Separations and Chiral Recognition Enantioselective Synthesis, Enantiomeric Separations and Chiral Recognition Special Issue Editors Maria Elizabeth Tiritan Madalena Pinto Carla Sofia Garcia Fernandes MDPI • Basel • Beijing • Wuhan • Barcelona • Belgrade • Manchester • Tokyo • Cluj • Tianjin Special Issue Editors Maria Elizabeth Tiritan Madalena Pinto Carla Sofia Garcia Fernandes Cooperativa de Ensino Superior Universidade do Porto Universidade do Porto Politecnico´ e Universitario´ (CESPU) Portugal Portugal Universidade do Porto Portugal Editorial Office MDPI St. Alban-Anlage 66 4052 Basel, Switzerland This is a reprint of articles from the Special Issue published online in the open access journal Molecules (ISSN 1420-3049) (available at: https://www.mdpi.com/journal/molecules/special issues/Chiral separation recognition). For citation purposes, cite each article independently as indicated on the article page online and as indicated below: LastName, A.A.; LastName, B.B.; LastName, C.C. Article Title. Journal Name Year, Article Number, Page Range. ISBN 978-3-03936-238-7 (Hbk) ISBN 978-3-03936-239-4 (PDF) Cover image courtesy of Maria Elizabeth Tiritan. c 2020 by the authors. Articles in this book are Open Access and distributed under the Creative Commons Attribution (CC BY) license, which allows users to download, copy and build upon published articles, as long as the author and publisher are properly credited, which ensures maximum dissemination and a wider impact of our publications. The book as a whole is distributed by MDPI under the terms and conditions of the Creative Commons license CC BY-NC-ND. Contents About the Special Issue Editors ..................................... vii Preface to ”Enantioselective Synthesis, Enantiomeric Separations and Chiral Recognition” .. ix Maria Elizabeth Tiritan, Madalena Pinto and Carla Fernandes Enantioselective Synthesis, Enantiomeric Separations and Chiral Recognition Reprinted from: Molecules 2020, 25, 1713, doi:10.3390/molecules25071713 .............. 1 Diana Ibrahim and Ashraf Ghanem On the Enantioselective HPLC Separation Ability of Sub-2 μm Columns: Chiralpak R IG-U and ID-U Reprinted from: Molecules 2019, 24, 1287, doi:10.3390/molecules24071287 .............. 7 Ali Fouad, Montaser Sh. A. Shaykoon, Samy M. Ibrahim, Sobhy M. El-Adl and Ashraf Ghanem Colistin Sulfate Chiral Stationary Phase for the Enantioselective Separation of Pharmaceuticals Using Organic Polymer Monolithic Capillary Chromatography Reprinted from: Molecules 2019, 24, 833, doi:10.3390/molecules24050833 .............. 19 Anamarija Knezevi´ˇ c, Jurica Novak and Vladimir Vinkovi´c New Brush-Type Chiral Stationary Phases for Enantioseparation of Pharmaceutical Drugs Reprinted from: Molecules 2019, 24, 823, doi:10.3390/molecules24040823 .............. 35 Lie-Ding Shiau Chiral Separation of the Phenylglycinol Enantiomers by Stripping Crystallization Reprinted from: Molecules 2018, 23, 2901, doi:10.3390/molecules23112901 .............. 51 Andreea Elena Bodoki, Bogdan-Cezar Iacob, Laura Elena Gliga, Simona Luminita Oprean, David A. Spivak, Nicholas A. Gariano and Ede Bodoki Improved Enantioselectivity for Atenolol Employing Pivot Based Molecular Imprinting Reprinted from: Molecules 2018, 23, 1875, doi:10.3390/molecules23081875 .............. 63 Joana Teixeira, Maria Elizabeth Tiritan, Madalena M. M. Pinto and Carla Fernandes Chiral Stationary Phases for Liquid Chromatography: Recent Developments Reprinted from: Molecules 2019, 24, 865, doi:10.3390/molecules24050865 .............. 83 Yangfeng Peng, Cai Feng, Sohrab Rohani and Quan He Improved Resolution of 4-Chloromandelic Acid and the Effect of Chlorine Interactions Using (R)-(+)-Benzyl-1-Phenylethylamine as a Resolving Agent Reprinted from: Molecules 2018, 23, 3354, doi:10.3390/molecules23123354 ..............121 Fei Xiong, Bei-Bei Yang, Jie Zhang and Li Li Enantioseparation, Stereochemical Assignment and Chiral Recognition Mechanism of Sulfoxide-Containing Drugs Reprinted from: Molecules 2018, 23, 2680, doi:10.3390/molecules23102680 ..............133 Yuichi Uwai Enantioselective Drug Recognition by Drug Transporters Reprinted from: Molecules 2018, 23, 3062, doi:10.3390/molecules23123062 ..............145 v Ankur Gogoi, Nirmal Mazumder, Surajit Konwer, Harsh Ranawat, Nai-Tzu Chen and Guan-Yu Zhuo Enantiomeric Recognition and Separation by Chiral Nanoparticles Reprinted from: Molecules 2019, 24, 1007, doi:10.3390/molecules24061007 ..............159 Giovanna Brancatelli, Enrico Dalcanale, Roberta Pinalli and Silvano Geremia Probing the Structural Determinants of Amino Acid Recognition: X-Ray Studies of Crystalline Ditopic Host-Guest Complexes of the Positively Charged Amino Acids, Arg, Lys, and His with a Cavitand Molecule Reprinted from: Molecules 2018, 23, 3368, doi:10.3390/molecules23123368 ..............191 Allan Ribeiro da Silva, Deborah Araujo dos Santos, Marcio Weber Paix˜ao and Arlene Gon¸calves Corrˆea Stereoselective Multicomponent Reactions in the Synthesis or Transformations of Epoxides and Aziridines Reprinted from: Molecules 2019, 24, 630, doi:10.3390/molecules24030630 ..............203 Farid Chebrouk, Khodir Madani, Brahim Cherfaoui, Leila Boukenna, M´onica V´alega, Ricardo F. Mendes, Filipe A. A. Paz, Khaldoun Bachari, Oualid Talhi and Artur M. S. Silva Hemi-Synthesis of Chiral Imine, Benzimidazole and Benzodiazepines from Essential Oil of Ammodaucus leucotrichus subsp. leucotrichus Reprinted from: Molecules 2019, 24, 975, doi:10.3390/molecules24050975 ..............227 Solida Long, Diana I. S. P. Resende, Anake Kijjoa, Artur M. S. Silva, Ricardo Fernandes, Cristina P. R. Xavier, M. Helena Vasconcelos, Em´ılia Sousa and Madalena M. M. Pinto Synthesis of New Proteomimetic Quinazolinone Alkaloids and Evaluation of Their Neuroprotective and Antitumor Effects Reprinted from: Molecules 2019, 24, 534, doi:10.3390/molecules24030534 ..............237 Jinsong Xuan and Yingang Feng Enantiomeric Tartaric Acid Production Using cis-Epoxysuccinate Hydrolase: History and Perspectives Reprinted from: Molecules 2019, 24, 903, doi:10.3390/molecules24050903 ..............255 Carla Fernandes, Maria Let´ıcia Carraro, Jo˜ao Ribeiro, Joana Araujo, ´ Maria Elizabeth Tiritan and Madalena M. M. Pinto Synthetic Chiral Derivatives of Xanthones: Biological Activities and Enantioselectivity Studies Reprinted from: Molecules 2019, 24, 791, doi:10.3390/molecules24040791 ..............267 Anna Poryvai, Terezia Vojtylov´a-Jurkoviˇcov´a, Michal Smahel,ˇ Natalie Kolderov´a, Petra Tom´aˇskov´a, David Sykora´ and Michal Kohout Determination of Optical Purity of Lactic Acid-Based Chiral Liquid Crystals and Corresponding Building Blocks by Chiral High-Performance Liquid Chromatography and Supercritical Fluid Chromatography Reprinted from: Molecules 2019, 24, 1099, doi:10.3390/molecules24061099 ..............303 Emilija Petronijevic and Concita Sibilia Enhanced Near-Field Chirality in Periodic Arrays of Si Nanowires for Chiral Sensing Reprinted from: Molecules 2019, 24, 853, doi:10.3390/molecules24050853 ..............315 Bang-Jin Wang, Ai-Hong Duan, Jun-Hui Zhang, Sheng-Ming Xie, Qiu-E Cao and Li-Ming Yuan An Enantioselective Potentiometric Sensor for 2-Amino-1-Butanol Based on Chiral Porous Organic Cage CC3-R Reprinted from: Molecules 2019, 24, 420, doi:10.3390/molecules24030420 ..............325 vi About the Special Issue Editors Maria Elizabeth Tiritan has a degree in chemistry and PhD in organic chemistry. Currently, she is Assistant Professor at the Faculty of Pharmacy of University of Porto and Team Leader of the Drug Research line at IINFACTS. Her current interests in research include exploiting new enantioselective analytical methods to quantify and identify metabolites in the biodegradation of chiral drugs in environmental matrices; synthesis of new chiral compounds for diverse biological activities, including potential antitumor and antimicrobial agents; as well as structure–activity–properties relationships. She is also involved in the design of new chiral selectors for enantiomeric separation by liquid chromatography and membranes. https://orcid.org/0000-0003-3320-730X; https://sigarra.up.pt/ffup/pt/func geral.formview?p codigo=481977; https://iinfacts.cespu.pt/. Madalena Pinto is a retired Full Professor from the Faculty of Pharmacy (FFUP) and Researcher and Team Leader of the Group of Natural Products and Medicinal Chemistry at the Interdisciplinary Center for Marine and Environmental Research (CIIMAR) University of Porto, Portugal. Her research areas focus on medicinal chemistry, involving the synthesis and molecular modification of pharmacologically active compounds based on natural models of plant and marine sources, as well as the development of substances with antifouling activity. She has a special interest in chirality, namely in synthesis and bioenantioselectivity studies of chiral bioactive compounds, as well as studies of structure–activity–properties relationships; molecular recognition of artificial receptors as new chiral stationary phases for liquid chromatography is another area of interest. ORCID: http://orcid.org/0000-0002-4676-1409;
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