ChiralityPub Date : 2024-02-27DOI: 10.1002/chir.23658
Jianwei Wu, Chuanwen Lin, Dan Liu, Qinghua Bian, Min Wang, Jiangchun Zhong
{"title":"Total synthesis of (6R,12R)-6,12-dimethylpentadecan-2-one, the sex pheromone of Diabrotica balteata LeConte","authors":"Jianwei Wu, Chuanwen Lin, Dan Liu, Qinghua Bian, Min Wang, Jiangchun Zhong","doi":"10.1002/chir.23658","DOIUrl":"10.1002/chir.23658","url":null,"abstract":"<p><i>Diabrotica balteata</i> LeConte is one of the most important polyphagous agricultural pests. The sex pheromone of this pest was synthesized using Evans asymmetric alkylation, ring-opening reaction of (<i>R</i>)-2-methyloxirane, S<sub>N</sub>2 alkylation of secondary tosylate, and coupling of chiral tosylate with Grignard reagent as central strategies. The sex pheromone prepared herein would be useful to control <i>D. balteata</i>.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 3","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139982500","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Chiral recognition and discrimination studies of tyrosine enantiomers on (−)-18-crown-6-tetracarboxylic acid as a chiral selector by nuclear magnetic resonance spectroscopy and docking simulations","authors":"Gaeun Lee, Suraj Adhikari, Sunho Lee, Jeong Yeon Lee, Yun-Cheol Na, Wonjae Lee, Eunjung Bang","doi":"10.1002/chir.23656","DOIUrl":"10.1002/chir.23656","url":null,"abstract":"<p>Considering the substantial significance of chiral biomolecules, such as amino acids, in our daily routines, we performed chiral recognition and discrimination of tyrosine (Tyr) enantiomers on (−)-(18-crown-6)-2,3,11,12-tetracarboxylic acid [(−)-18-C-6-TA] as crown-ether type chiral selector (CS) by nuclear magnetic resonance (NMR) spectroscopy and docking simulations. In this study, successful discrimination of the enantiomers of Tyr was achieved, as evidenced by the proton chemical shift differences (ΔΔδ) of Tyr enantiomers observed in the <sup>1</sup>H NMR spectra with (−)-18-C-6-TA CS. We compared the results of these two techniques with the findings obtained from high performance liquid chromatography (HPLC) investigations. In both NMR and HPLC experimental and docking simulation studies, a stronger interaction between the L-Tyr enantiomer with (−)-18-C-6-TA CS than the D-Tyr was consistently observed. Also, the binding energy differences (ΔΔE<sub>L-D</sub>) found in simulation data that correspond to enantioselectivity aligned well with the NMR experimental result.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 3","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139971077","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ChiralityPub Date : 2024-02-26DOI: 10.1002/chir.23649
Marco Fusè, Giuseppe Mazzeo, Sergio Abbate, Renzo Ruzziconi, Julien Bloino, Giovanna Longhi
{"title":"Mid-IR and CH stretching vibrational circular dichroism spectroscopy to distinguish various sources of chirality: The case of quinophaneoxazoline based ruthenium(II) complexes","authors":"Marco Fusè, Giuseppe Mazzeo, Sergio Abbate, Renzo Ruzziconi, Julien Bloino, Giovanna Longhi","doi":"10.1002/chir.23649","DOIUrl":"10.1002/chir.23649","url":null,"abstract":"<p>Five diastereomers of ruthenium(II) complexes based on quinolinophaneoxazoline ligands were investigated by vibrational circular dichroism (VCD) in the mid-IR and CH stretching regions. Diastereomers differ in three sources of chirality: the planar chirality of the quinolinophane moiety, the central chirality of an asymmetric carbon atom of the oxazoline ring, and the chirality of the ruthenium atom. VCD, allied to DFT calculations, has been found to be effective in disentangling the various forms of chirality. In particular, a VCD band is identified in the CH stretching region directly connected to the chirality of the metal. The analysis of the calculated VCD spectra is carried out by partitioning the complexes into fragments. The anharmonic analysis is also performed with a recently proposed reduced-dimensionality approach: such treatment is particularly important when examining spectroscopic regions highly perturbed by resonances, like the CH stretching region.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 3","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139971078","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ChiralityPub Date : 2024-02-25DOI: 10.1002/chir.23653
Liao Youyin, Ma Yuexing, Chen Jiahao, Qian Kun, Yang Jie, Pan Rongbin, Xu Yiyong
{"title":"Study on the anti-cancer activity of α-phenethylamine ferrocenecarboxylic acid co-crystals","authors":"Liao Youyin, Ma Yuexing, Chen Jiahao, Qian Kun, Yang Jie, Pan Rongbin, Xu Yiyong","doi":"10.1002/chir.23653","DOIUrl":"10.1002/chir.23653","url":null,"abstract":"<p>Ferrocene derivatives show a wide range of pharmacological activities in the medical field, especially in the anti-tumor field, and can be used as candidate drugs or lead compounds for the treatment of tumors and other diseases. And <i>α</i>-phenethylamine is an important intermediate for the preparation of fine chemical products. (<i>R</i>)-(+)-1-Phenethylamine ferrocenecarboxylic acid/(<i>S</i>)-(−)-1-phenethylamine ferrocenecarboxylic acid were prepared, named compounds <b>1</b> and <b>2</b>, respectively. Single crystal X-ray diffraction showed that compounds <b>1</b> and <b>2</b> crystallized in the orthorhombic system space group <i>P</i>2<sub>1</sub>2<sub>1</sub>2<sub>1</sub>, and the crystal structures of compounds <b>1</b> and <b>2</b> exhibited mirror symmetry. The inhibitory effect of two compounds on SW480, MDA-MB-231, and H1299 cells was tested by MTT colorimetry. The IC<sub>50</sub> values of the compounds against cancer cells were also calculated. The anti-cancer effect was more pronounced for compounds in the <i>S</i>-configuration. Compound <b>2</b> made the wild-type cancer cells undergo apoptosis, thus preventing cancer; it also had the function of helping the cell gene repair defects.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 3","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139968779","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ChiralityPub Date : 2024-02-21DOI: 10.1002/chir.23650
{"title":"Correction to “Effect of chirality in the supramolecular polymerization of N-annulated perylenediimides: Cancelling pathway complexity”","authors":"","doi":"10.1002/chir.23650","DOIUrl":"https://doi.org/10.1002/chir.23650","url":null,"abstract":"<p>\u0000 <span>Greciano, EE</span>, <span>Schwalb, AJ</span>, <span>Sánchez, L</span>. <span>Effect of chirality in the supramolecular polymerization of N-annulated perylenediimides: cancelling pathway complexity</span>. <i>Chirality</i>. <span>2024</span>; <span>36</span>(<span>2</span>):e23639. doi:10.1002/chir.23639\u0000 </p><p>This article was published ahead of its designation as a themed special issue article and was intended to contain a note saying that it will be published as part of the special issue for “Proceedings from 33<sup>rd</sup> Symposium on Chirality in Rome, Italy 2023.”</p><p>We apologize for this error.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 2","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.23650","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139915739","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ChiralityPub Date : 2024-02-21DOI: 10.1002/chir.23651
{"title":"Correction to “Switching the on-surface orientation of oxygen-functionalized helicene”","authors":"","doi":"10.1002/chir.23651","DOIUrl":"https://doi.org/10.1002/chir.23651","url":null,"abstract":"<p>\u0000 <span>Voigt, J</span>, <span>Hasan, M</span>, <span>Wäckerlin, C</span>, <span>Karnik, AV</span>, <span>Ernst, K-H</span>. <span>Switching the on-surface orientation of oxygen-functionalized helicene</span>. <i>Chirality</i>. <span>2024</span>; <span>36</span>(<span>2</span>):e23642. https://doi.org/10.1002/chir.23642\u0000 </p><p>This article was published ahead of its designation as a themed special issue article and was intended to contain a note saying that it will be published as part of the special issue for “Proceedings from 33<sup>rd</sup> Symposium on Chirality in Rome, Italy 2023.”</p><p>We apologize for this error.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 2","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.23651","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139915648","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ChiralityPub Date : 2024-02-14DOI: 10.1002/chir.23647
Vinod Kumar Vashistha, Tarun Kumar, Suman Yadav, Dipak Kumar Das
{"title":"Enantioselective separation and determination of ibuprofen: Stereoselective pharmacokinetics, pharmacodynamics and analytical methods","authors":"Vinod Kumar Vashistha, Tarun Kumar, Suman Yadav, Dipak Kumar Das","doi":"10.1002/chir.23647","DOIUrl":"10.1002/chir.23647","url":null,"abstract":"<p>Ibuprofen (IBP), the 29th most prescribed drug in the United States in 2019, is a widely used nonsteroidal anti-inflammatory drug (NSAID) comprising two enantiomers, (<i>R</i>)-IBP and (<i>S</i>)-IBP, collectively known as (<i>RS</i>)-IBP. This critical review examines analytical techniques for the enantioselective separation and determination of IBP enantiomers, crucial for pharmaceutical and clinical applications. The review focuses on state-of-the-art methods, including chromatographic techniques including high-performance liquid chromatography, gas chromatography, liquid chromatography–tandem mass spectrometry, and some other techniques. This review addresses pharmacokinetics, pharmacology, and side effects of each enantiomer, ensuring safe drug usage. By consolidating diverse analytical methods and their applicability in different matrices, this review serves as a valuable resource for researchers, analysts, and practitioners in pharmaceutical analysis, pharmacology, and clinical studies.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 2","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139734634","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ChiralityPub Date : 2024-02-14DOI: 10.1002/chir.23644
Qingli Zeng, Zhiqin Huang, Dan Li, Laisheng Li
{"title":"Preparation of a bis-triazolyl bridged β-cyclodextrin stationary phase and its application for enantioseparation of chiral compounds by HPLC","authors":"Qingli Zeng, Zhiqin Huang, Dan Li, Laisheng Li","doi":"10.1002/chir.23644","DOIUrl":"10.1002/chir.23644","url":null,"abstract":"<p>A novel <i>bis</i>-triazolyl bridged β-cyclodextrin was first synthesized by the Click reaction between azido-β-cyclodextrin and 1,6-heptadiyne. Then it was bonded onto silica gel to obtain a <i>bis</i>-triazolyl bridged β-cyclodextrin-based chiral stationary phase (BCDP). After structure characterization, the HPLC performance of BCDP was systematically evaluated by using different types of compounds as probes. The results showed that BCDP could well separate 18 kinds of achiral aromatic compounds (homologues, positional isomers, etc.) and 35 kinds of chiral drugs or pesticides, such as triazoles (<i>R</i>s = 1.33–3.15), flavanones (<i>R</i>s = 1.49–2.62), dansyl amino acids (<i>R</i>s = 0.96–1.99), and β-blocker drugs (<i>R</i>s = 0.68–2.78). BCDP could separate a wider range of compounds (53 kinds); especially, some chiral substance pairs that were difficult to be resolved on the ordinary cyclodextrin CSPs, including triazoles containing two chiral carbons (triadimenol, bitertanol, metconazole, and triticonazole), strongly ionized amino acids (acidic Asp, alkalic Arg, and polar Thr) and β-blockers with bulky groups (carvedilol, propranolol, and pindolol). Obviously, the unique synergistic inclusion effect of bridged cyclodextrin with double cavities and the <i>bis</i>-triazole bridging group could provide multiple action sites, such as hydrogen bonding, π-π stacking and acid–base action sites, thus improving its chiral chromatographic performance.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 2","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139729119","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ChiralityPub Date : 2024-02-14DOI: 10.1002/chir.23646
Martin Paškan, Kristýna Dobšíková, Martin Kuchař, Vladimír Setnička, Michal Kohout
{"title":"Synthesis and absolute configuration of cyclic synthetic cathinones derived from α-tetralone","authors":"Martin Paškan, Kristýna Dobšíková, Martin Kuchař, Vladimír Setnička, Michal Kohout","doi":"10.1002/chir.23646","DOIUrl":"10.1002/chir.23646","url":null,"abstract":"<p>The emergence of new synthetic cathinones continues to be a matter of public health concern. In fact, already known products (drugs) are being rapidly replaced by new structurally related alternatives, whereby modifications in the basic cathinone structure are used by manufacturers to circumvent the legislation. On the other hand, some derivatives of synthetic cathinones represent important pharmaceuticals with antidepressant properties. In the search for pharmaceutically relevant analogs, the main goal of the present study was to design and characterize novel cyclic α-tetralone-based derivatives of synthetic cathinones. We synthesized a series of derivatives and verified their chemical structure. Subsequently, chiral separation has been accomplished by high-performance liquid chromatography (HPLC) equipped with a circular dichroism (CD) detector, which directly provided CD spectra of the enantiomers of the analyzed substances at 252 nm. Using density functional theory calculations, we have obtained stable conformers of selected enantiomers in solution and their relative abundances, which we used to simulate their spectra. The experimental and calculated data have been used to assign the absolute configuration of six as-yet unknown synthetic cathinones.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 2","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.23646","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139729120","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ChiralityPub Date : 2024-02-07DOI: 10.1002/chir.23645
May Abdullah Abomuti
{"title":"Chiral acidic molecularly imprinted polymer for enantio-separation of norepinephrine racemate","authors":"May Abdullah Abomuti","doi":"10.1002/chir.23645","DOIUrl":"https://doi.org/10.1002/chir.23645","url":null,"abstract":"<p>We are looking into how well a copolymeric material made of poly (maleic acid–co-4-vinylpyridine) cross-linked with divinylbenzene can separate L-norepinephrine (L-NEP) from (±)-NEP. The initial step in this direction was the synthesis and subsequent analysis of L-NEP-maleimide chiral derivative. A 4-vinylpyridine/divinylbenzene combination was copolymerized with the resultant chiral maleimide. After heating the polymer materials in a high-alkaline environment to breakdown the connecting imide bonds, they were acidified in an HCl solution to eliminate the incorporated L-NEP species. Fourier transform infrared spectroscopy (FTIR) and a scanning electron microscope were used to examine the imprinted L-NEP-imprinted materials. The manufactured L-NEP-imprinted materials exhibited selectivity characteristics that were over 11 times greater for L-NEP than D-norepinephrine. The highest capacity observed in Langmuir adsorption studies was 170 mg/g at a pH of 7. After optical separation using a column technique, it was determined that the enantiomeric excess levels of D-norepinephrine and L-NEP in the first feeding and subsequent recovery solutions were 95% and 81%, respectively.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 2","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139700647","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}