Chirality最新文献

{"title":"Enantioselective high-performance liquid chromatography combined with spectroscopic methods and theoretical calculations: A valid strategy to determine the absolute configuration of eugenol derivatives","authors":"Simone Manetto,&nbsp;Giulia Mazzoccanti,&nbsp;Gaia Pulitelli,&nbsp;Sofia Niccolai,&nbsp;Damiano Tanini,&nbsp;Marco Pierini,&nbsp;Roberto Cirilli","doi":"10.1002/chir.23668","DOIUrl":"10.1002/chir.23668","url":null,"abstract":"<p>The absolute configuration of three chiral eugenol derivatives was assigned by a multi-step methodology based on enantioselective HPLC combined with spectroscopic and theoretical calculations. Milligram amounts of enantiopure forms used for stereochemical characterization were isolated by HPLC on the immobilized amylose-based chiral stationary phase Chiralpak IG using normal phase elution conditions. The absolute configuration was indirectly determined for one of the three compounds by ¹H NMR via methoxy-α-trifluoromethyl-α-phenylacetic acid derivatization (Mosher's acid). Comparison of the experimental and predicted electronic circular dichroism spectra confirmed the stereochemical assignment by Mosher's method and extended the absolute configuration assignment to two other chiral compounds.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 5","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140920768","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":"Screening of Astec® CHIRALDEX™ G-PN and LIPODEX™ D gas chromatography columns for enantioseparation of amphetamine derivatives","authors":"Eva-Maria Hubner,&nbsp;Sophie Schützinger,&nbsp;Katarína Molnárová,&nbsp;Martin G. Schmid","doi":"10.1002/chir.23676","DOIUrl":"10.1002/chir.23676","url":null,"abstract":"<p>Among different substance classes, New Psychoactive Substances (NPS) comprise chiral amphetamines for stimulant and empathic effects. There is little knowledge in terms of clinical studies about possibly different effects of the two enantiomers of novel amphetamine derivatives. For this reason, there is a big demand for enantioseparation method development of this new substance class.</p><p>Regarding gas chromatography, cyclodextrins proved to be effective for enantioseparation of NPS. In our attempt, an Astec® Chiraldex™ G-PN column containing 2,6-di-O-pentyl-3-propionyl-γ-cyclodextrin and a Lipodex™ D column containing heptakis-(2,6-di-O-pentyl-O-acetyl)-β-cyclodextrin as chiral selector served as stationary phases in a Shimadzu GCMS-QP2010 SE system.</p><p>Because of the special coating, maximum temperature is limited to 200 °C isothermal or 220 °C in programmed mode. To ensure detection, trifluoroacetic anhydride (TFAA) was used to increase sample volatility.¹ As a result, 35 amphetamines were tested as their TFAA-derivatives.</p><p>A screening method with a temperature gradient from 140 °C to 200 °C at a heating ramp of 1 °C per minute and final time of 5 min, showed baseline separation for seven and partial separations for 16 trifluoro acetylated amphetamines using the Chiraldex™ G-PN column. Six baseline and nine partial separations were observed with the Lipodex™ D column, respectively.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 5","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-05-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.23676","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140911268","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}

{"title":"Chiroptically active copper clusters as platform for enantioselective detection of lysine","authors":"Camelia Dutta,&nbsp;Ragul Vivaz Nataraajan,&nbsp;Jatish Kumar","doi":"10.1002/chir.23670","DOIUrl":"10.1002/chir.23670","url":null,"abstract":"<p>Metal clusters have drawn considerable research attention over the years due to their fascinating optical properties. Owing to their appealing photophysical characteristics, these materials have drawn attention as potential candidates for various application in diverse fields, including disease detection, biosensing, chemical sensing, and the fabrication of light-harvesting materials. Presently, there is an increasing research focus on the use of clusters in biomedical research, both as biodetection platform and as bioimaging agents. Of special interest are chiral clusters, which can selectively interact with chiral biomolecules owing to their optical activity. Herein, we showcase the use of a pair of chiroptically active copper clusters for the enantioselective detection of lysine, an amino acid of vast biological relevance. Two techniques are concurrently employed for the detection of lysine at varying concentrations. Circular dichroism serves as a potent tool for detecting lysine at low concentrations, whereas luminescence is effectively employed as a detection method for high analyte concentrations. The combined electronic impact of clusters and lysine resulted in the emergence of an enhanced enantioselective Cotton effect at specific wavelength.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 5","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140875979","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":"Circular dichroism spectrum of (R)-(+)-3,3′-dibromo-1,1′-bi-2-naphthol in albumin: Alterations caused by complexation—Experimental and in silico investigation","authors":"Valdecir Farias Ximenes,&nbsp;Maurício Ikeda Yoguim,&nbsp;Aguinaldo Robinson de Souza,&nbsp;Nelson Henrique Morgon","doi":"10.1002/chir.23675","DOIUrl":"https://doi.org/10.1002/chir.23675","url":null,"abstract":"<p>This study describes the interaction of human serum albumin (HSA) with the binol derivative (<i>R</i>)-(+)-3,3′-dibromo-1,1′-bi-2-naphthol (<i>R-BrB</i>), which has its optical activity based on the prohibitive energetic barrier for conversion into the enantiomer (<i>S</i>)-(+)-3,3′-dibromo-1,1′-bi-2-naphthol (<i>S-BrB</i>). The objective was to assess the ability of HSA to differentiate axial enantiomers based on their binding efficiency and their impact on the CD spectra. We discovered that both enantiomers were effective ligands, and the CD signal disappeared when equimolar amounts of <i>R-BrB</i> and <i>S-BrB</i> were simultaneously added, indicating no preference for either enantiomer. The complexation resulted in a significant signal increase at 250 nm and a bathochromic effect at 370 nm. Molecular docking simulations were performed, and the lower energy pose of <i>R-BrB</i> was selected for DFT calculations. The theoretical CD spectra of free and complexed <i>R-BrB</i> were obtained and showed alterations corroborating the experimental results. By comparing the difference spectrum (HSA:<i>R-BrB</i> minus HSA) with the spectrum of free <i>RBrB</i> in water or ethyl alcohol, we concluded that the CD signal intensification was due to the increased solubilization of <i>R-BrB</i> upon binding to HSA.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 5","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140820629","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":"Enantiomeric separation of tryptophan via novel chiral polyamide composite membrane","authors":"Xinwei Peng,&nbsp;Yongming Wei,&nbsp;Yangfeng Peng,&nbsp;Hongliang Zhao,&nbsp;Tianzhong Tong,&nbsp;Quan He","doi":"10.1002/chir.23674","DOIUrl":"https://doi.org/10.1002/chir.23674","url":null,"abstract":"<p>The separation of chiral drugs continues to pose a significant challenge. However, in recent years, the emergence of membrane-based chiral separation has shown promising effectiveness due to its environmentally friendly, energy-efficient, and cost-effective characteristics. In this study, we prepared chiral composite membrane via interfacial polymerization (IP), utilizing β-cyclodextrin (β-CD) and piperazine (PIP) as mixed monomers in the aqueous phase. The chiral separation process was facilitated by β-CD, serving as a chiral selective agent. The resulting membrane were characterized using SEM, FT-IR, and XPS. Subsequently, the chiral separation performance of the membrane for DL-tryptophan (Trp) was investigated. Lastly, the water flux, dye rejection, and stability of the membrane were also examined. The results showed that the optimized chiral PIP_0.5β-CD_0.5 membrane achieved an enantiomeric excess percentage (ee%) of 43.0% for D-Trp, with a solute flux of 66.18 nmol·cm⁻²·h⁻¹, and maintained a good chiral separation stability. Additionally, the membrane demonstrated positive performance in the selective separation of mixed dyes, allowing for steady operation over a long period of time. This study offers fresh insights into membrane-based chiral separations.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 5","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140820628","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":"Impact of helical elongation of symmetric oxa[n]helicenes on their structural, photophysical, and chiroptical characteristics","authors":"Mohamed S. H. Salem,&nbsp;Rubal Sharma,&nbsp;Seika Suzuki,&nbsp;Yoshitane Imai,&nbsp;Mitsuhiro Arisawa,&nbsp;Shinobu Takizawa","doi":"10.1002/chir.23673","DOIUrl":"https://doi.org/10.1002/chir.23673","url":null,"abstract":"<p>The adjustment of the main helical scaffold in helicenes is a fundamental strategy for modulating their optical features, thereby enhancing their potential for diverse applications. This work explores the influence of helical elongation (n = 5–9) on the structural, photophysical, and chiroptical features of symmetric oxa[<i>n</i>]helicenes. Crystal structure analyses revealed structural variations with helical extension, impacting torsion angles, helical pitch, and packing arrangements. Through theoretical investigations using density functional theory (DFT) calculations, the impact of helical extension on aromaticity, planarity distortion, and heightened chiral stability were discussed. Photophysical features were studied through spectrophotometric analysis, with insights gained through time-dependent DFT (TD-DFT) calculations. Following optical resolution via chiral high-performance liquid chromatography (HPLC), the chiroptical properties of both enantiomers of oxa[7]helicene and oxa[9]helicene were investigated. A slight variation in the main helical scaffold of oxa[<i>n</i>]helicenes from [7] to [9] induced an approximately three-fold increase in dissymmetry factors with the biggest values of|<i>g</i>_<i>lum</i>| of oxa[9]helicene (2.2 × 10⁻³) compared to|<i>g</i>_<i>lum</i>|of oxa[7]helicene (0.8 × 10⁻³), findings discussed and supported by TD-DFT calculations.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 5","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-05-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.23673","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140820511","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}

{"title":"New methods for resolution of hydroxychloroquine by forming diastereomeric salt and adding chiral mobile phase agent on RP-HPLC","authors":"Chen Chen,&nbsp;Yangfeng Peng,&nbsp;Yongming Wei,&nbsp;Mengyuan Liu,&nbsp;Yu Wang,&nbsp;Siqi Xiong,&nbsp;Huiyi Li,&nbsp;Quan He","doi":"10.1002/chir.23672","DOIUrl":"https://doi.org/10.1002/chir.23672","url":null,"abstract":"&lt;p&gt;Hydroxychloroquine (HCQ), 2-([4-([7-Chloro-4-quinolyl]amino)pentyl]ethylamino)ethanol, exhibited significant biological activity, while its side effects cannot be overlooked. The RP-HPLC enantio-separation was investigated for cost-effective and convenient optical purity analysis of HCQ. The thermodynamic resolution of Rac-HCQ, driven by enthalpy and entropy, was achieved on the C18 column using Carboxymethyl-β-cyclodextrin (CM-β-CD) as the chiral mobile phase agent (CMPA). The effects of C&lt;sub&gt;CM-β-CD&lt;/sub&gt;, pH, and triethylamine (TEA) V% on the enantio-separation process were explored. Under the optimum conditions at 24°C, the retention times for the two enantiomers were &lt;span&gt;&lt;/span&gt;&lt;math&gt;\u0000 &lt;semantics&gt;\u0000 &lt;mrow&gt;\u0000 &lt;msub&gt;\u0000 &lt;mi&gt;t&lt;/mi&gt;\u0000 &lt;mrow&gt;\u0000 &lt;mi&gt;R&lt;/mi&gt;\u0000 &lt;mn&gt;1&lt;/mn&gt;\u0000 &lt;/mrow&gt;\u0000 &lt;/msub&gt;\u0000 &lt;mo&gt;=&lt;/mo&gt;\u0000 &lt;mn&gt;29.39&lt;/mn&gt;\u0000 &lt;mspace&gt;&lt;/mspace&gt;\u0000 &lt;mi&gt;min&lt;/mi&gt;\u0000 &lt;/mrow&gt;\u0000 &lt;annotation&gt;$$ {t}_{R1}=29.39 min $$&lt;/annotation&gt;\u0000 &lt;/semantics&gt;&lt;/math&gt; and &lt;span&gt;&lt;/span&gt;&lt;math&gt;\u0000 &lt;semantics&gt;\u0000 &lt;mrow&gt;\u0000 &lt;msub&gt;\u0000 &lt;mi&gt;t&lt;/mi&gt;\u0000 &lt;mrow&gt;\u0000 &lt;mi&gt;R&lt;/mi&gt;\u0000 &lt;mn&gt;2&lt;/mn&gt;\u0000 &lt;/mrow&gt;\u0000 &lt;/msub&gt;\u0000 &lt;mo&gt;=&lt;/mo&gt;\u0000 &lt;mn&gt;32.42&lt;/mn&gt;\u0000 &lt;mspace&gt;&lt;/mspace&gt;\u0000 &lt;mi&gt;min&lt;/mi&gt;\u0000 &lt;/mrow&gt;\u0000 &lt;annotation&gt;$$ {t}_{R2}=32.42 min $$&lt;/annotation&gt;\u0000 &lt;/semantics&gt;&lt;/math&gt;, resulting in &lt;span&gt;&lt;/span&gt;&lt;math&gt;\u0000 &lt;semantics&gt;\u0000 &lt;mrow&gt;\u0000 &lt;msub&gt;\u0000 &lt;mi&gt;R&lt;/mi&gt;\u0000 &lt;mi&gt;s&lt;/mi&gt;\u0000 &lt;/msub&gt;\u0000 &lt;mo&gt;=&lt;/mo&gt;\u0000 &lt;mn&gt;1.87&lt;/mn&gt;\u0000 &lt;/mrow&gt;\u0000 &lt;annotation&gt;$$ {R}_s=1.87 $$&lt;/annotation&gt;\u0000 &lt;/semantics&gt;&lt;/math&gt;. The resolution via diastereomeric salt formation of Rac-HCQ was developed to obtain the active pharmaceutical ingredient of single enantiomer S-HCQ. Di-p-Anisoyl-L-Tartaric Acid (L-DATA) was proved effective as the resolution agent for Rac-HCQ. Surprisingly, it was found that refluxing time was a key fact affecting the resolution efficiency, which meant the kinetic dominate during the process of the resolution. Four factors—solvent volume, refluxing time, filtration temperature, and molar ratio—were optimized using the single-factor method and the response surface method. Two cubic models were established, and the reliability was subsequently verified. Under the optimal conditions, the less soluble salt of 2L-DATA:S-HCQ was obtained with a yield of 96.9% and optical purity of 63.0%. The optical purity of this less soluble salt increases to 99.0% with a yield of 74.2% after three ","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 5","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140818992","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":"Asymmetric catalysis by chiral FLPs: A computational mini-review","authors":"Shanti Gopal Patra","doi":"10.1002/chir.23671","DOIUrl":"https://doi.org/10.1002/chir.23671","url":null,"abstract":"<p>Steric hindrance in Lewis acid (LA) and Lewis base (LB) obstruct the Lewis acid–base adduct formation, and the pair was termed as frustrated Lewis pair (FLP). In the past 16 years, the field of enantioselective catalysis by chiral FLPs has been slowly growing. It was shown that chiral LAs are significant as they are involved in the hydrogen transfer (HT) step to the imine, resulting in enantioselectivity. After H₂ activation, the borohydride can exist in a number of plausible conformations and their stability is governed by the presence of noncovalent interaction through C–H····π and π····π interactions. However, LBs are not ideal for asymmetric induction as they compete with the imine substrate as a counter LB. Further, the proton transfer from chiral LB to the imine does not induce any chirality as chirality develops in the HT step. However, intramolecular FLPs with chiral scaffold are very efficient as they possess an optimum distance between LA and LB, which facilitates the H₂ activation but precludes the adduct formation of the small molecules substrate with the LA component. This mini-review summarizes computational investigation involving chiral LA and LB, and discusses intramolecular FLPs in the enantioselective catalysis.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 5","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140641768","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":"Advantages of a synchrotron light source for fluorescence-detected linear dichroism","authors":"Nykola C. Jones,&nbsp;Alison Rodger,&nbsp;Søren V. Hoffmann","doi":"10.1002/chir.23667","DOIUrl":"https://doi.org/10.1002/chir.23667","url":null,"abstract":"<p>Fluorescence-detected linear dichroism (FD-LD) enables one to collect linear dichroism spectra for oriented fluorophores in the presence of other absorbing species and light scattering. The experiment proceeds by scanning the excitation wavelength and using a filter to collect only emitted photons from the fluorophore. Thus, it has the potential to give data with enhanced selectivity and quality. By using a synchrotron radiation light source and fluorescence-detection, we show data for a range of fluorophores in different orienting environments. Film and flow-oriented FD-LD spectra were collected down to 170 nm. Even for flow-oriented liposomes, we have data collected down to 210 nm. For strongly scattering samples, for example, liposomes, FD-LD has the clear advantage that scattering is absent for the longer wavelength fluorescence photons. The collimated and smaller beam size of the synchrotron radiation also gives rise to sharper and more well-defined features in the spectra.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 4","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-04-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.23667","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140550032","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}

{"title":"Novel ethylenediamine-β-cyclodextrin grafted membranes for the chiral separation of mandelic acid and its derivatives","authors":"Junjie Zhou,&nbsp;Yongming Wei,&nbsp;Jiaojie Wu,&nbsp;Shuqin Li,&nbsp;Zhenliang Xu,&nbsp;Yangfeng Peng","doi":"10.1002/chir.23662","DOIUrl":"https://doi.org/10.1002/chir.23662","url":null,"abstract":"<p>In the present study, flat cellulose acetate ultrafiltration membranes were prepared first by nonsolvent induced phase separation method. Then chiral membranes for separating the enantiomers were prepared by grafting the ultrafiltration membranes using ethylenediamine-β-cyclodextrin as the chiral selector and epichlorohydrin as the spacer arm. The pure water permeability of the ultrafiltration membrane was around 115 L·m⁻²·h⁻¹·bar⁻¹. The properties of the chiral membranes were characterized using infrared spectroscopy (ATR-FTIR), X-ray photoelectron spectroscopy (XPS), and scanning electron microscopy (SEM). The chiral membrane performance in enantiomer separation was evaluated with racemates, such as mandelic acid (MA), 2-chloromandelic acid (2-ClMA), 4-chloromandelic acid (4-ClMA), and methyl mandelate (MM). The influence of feed concentration on the separation efficiency was also investigated. The results indicated that the enantiomeric excess percentages (e.e%) of the racemic mixtures for these four chiral compounds were up to 31.8%, 25.4%, 17.8%, and 32.6%, respectively. The binding free energy of the chiral selector with the (<i>S</i>)-enantiomer calculated by molecular dynamics simulations was stronger than that with the (<i>R</i>)-enantiomer, which was consistent with the experimental results (higher concentration of (<i>R</i>)-enantiomer in the permeate). This supports the affinity absorption-separation mechanism.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 4","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140345718","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}