IF 3 4区化学

Chirality Pub Date : 2025-10-02 DOI: 10.1002/chir.70051

Sergey V. Stovbun, Aleksey A. Skoblin, Dmitry V. Zlenko

{"title":"Cross-Catalysis and Weak Interactions: Keys to the Chiral Polarization of the Biosphere","authors":"Sergey V. Stovbun, Aleksey A. Skoblin, Dmitry V. Zlenko","doi":"10.1002/chir.70051","DOIUrl":"10.1002/chir.70051","url":null,"abstract":"<div>\u0000 \u0000 Molecular homochirality — the uniformity of chirality in biological molecules — is a fundamental feature of life, yet its origins remain unresolved. The correspondence between the chirality of biological monomers on Earth and that observed in ancient meteorites implies a systematic selection of chirality sign in prebiotic chemistry, rather than a stochastic process. While classical theories attribute symmetry breaking to chiral autocatalysis, such self-amplifying processes are rare and have not been empirically demonstrated in the synthesis of amino acids and carbohydrates. In contrast, chiral cross-catalysis between amino acids and carbohydrates — a mechanism consistent with known chemical behavior — could similarly amplify chiral purity. However, cross-catalysis alone cannot determine the chirality sign due to its inherent symmetry, leaving the origin of the initial bias unexplained. Although weak interactions have been proposed as a potential source of this bias, their effects are theoretically negligible, raising questions about their sufficiency. Our kinetic analysis of cross-catalytic systems reveals that even an infinitesimal preference for left-handed amino acids and right-handed carbohydrates could be sufficient to establish the homochirality observed in life. This mechanism provides a plausible link between prebiotic chemistry and the homochirality of the biosphere, offering a potential resolution to this longstanding enigma.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 10","pages":""},"PeriodicalIF":3.0,"publicationDate":"2025-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145205686","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}

引用次数: 0

Time-Dependent Resolution of an Atropisomeric 1-Arylpyrrole by a Novel 1-Arylethylamine Saltforming Agent 一种新型的1-芳乙胺盐化剂对atro二聚体1-芳基吡咯的时间依赖性拆分

IF 3 4区化学

Chirality Pub Date : 2025-10-01 DOI: 10.1002/chir.70054

Hong Ha Thuy Nguyen, Erika Bálint, Béla Mátravölgyi

{"title":"Time-Dependent Resolution of an Atropisomeric 1-Arylpyrrole by a Novel 1-Arylethylamine Saltforming Agent","authors":"Hong Ha Thuy Nguyen, Erika Bálint, Béla Mátravölgyi","doi":"10.1002/chir.70054","DOIUrl":"https://doi.org/10.1002/chir.70054","url":null,"abstract":"<div>\u0000 \u0000 This study represents a special, time-dependent resolution strategy of an atropisomeric, bifunctional 1-phenylpyrrole derivative, using the nonactive enantiomer of the key amine intermediate Apremilast as an efficient resolving agent. Among the solvents investigated, ethyl acetate was identified as the optimal solvent, allowing rapid crystallization and high enantiomeric purity (> 99% ee). A detailed study of kinetic behavior revealed that early-stage crystallization and timely separation of diastereomeric salt are critical to achieving high enantiopurity and avoiding recrystallization to lead to a racemic product. Time-dependent studies suggest that solvate formation of enantiomers and ethyl acetate plays a crucial role in the resolution mechanism. This resolution process enables the direct separation of racemic 2-(2-carbamoyl-1H-pyrrol-1-yl)-3-(trifluoromethyl) benzoic acid suitable for further applications, such as resolving agents for amine-type compounds. Significantly, this approach recycles an amine-type drug intermediate that is typically discarded during the large-scale production of Apremilast, thus being in line with green chemistry principles by minimizing waste and enabling resource recovery.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 10","pages":""},"PeriodicalIF":3.0,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145196459","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}

引用次数: 0

May Two Enantiomers Have Different Raman Spectra? 两个对映体可能有不同的拉曼光谱吗？

IF 3 4区化学

Chirality Pub Date : 2025-09-08 DOI: 10.1002/chir.70053

Gianluigi Albano, Gennaro Pescitelli

引用次数: 0

A Robust HPLC Method for the Simultaneous Determination of Finerenone and Its Enantiomer Using AQbD AQbD同时测定菲尼酮及其对映体的高效液相色谱方法

IF 3 4区化学

Chirality Pub Date : 2025-08-28 DOI: 10.1002/chir.70052

Badriah Saad Al-Farhan, Ghada M. G. Eldin

{"title":"A Robust HPLC Method for the Simultaneous Determination of Finerenone and Its Enantiomer Using AQbD","authors":"Badriah Saad Al-Farhan, Ghada M. G. Eldin","doi":"10.1002/chir.70052","DOIUrl":"https://doi.org/10.1002/chir.70052","url":null,"abstract":"<div>\u0000 \u0000 The enantiomeric purity of Finerenone (FIN), a novel therapeutic for chronic kidney disease (CKD), is a critical quality attribute for ensuring patient safety. This study reports the first chiral HPLC method for the simultaneous determination of FIN and its enantiomer, developed and validated using a rigorous analytical quality by design (AQbD) framework. The method employs a CHIRALPAK AD-H column with an isocratic mobile phase of n-hexane: ethanol (62:38, v/v). Optimized conditions provide excellent baseline resolution (Rₛ = 3.5) in under 10 min. The method was validated using accuracy profiles, demonstrating high performance with limits of quantification established at 340 μg mL−1 for FIN and 0.40 μg mL−1 for its 4R enantiomer. The AQbD approach successfully defined a robust method operable design region (MODR) to ensure consistent performance. Furthermore, a multimetric sustainability evaluation confirmed the method's favorable eco-profile, achieving a Grade Index (BAGI) score of 77.5 and Red-Green-Blue 12 (RGB12) score of 80.8. This work provides a reliable, robust, and eco-conscious analytical tool essential for the quality control of FIN formulations.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 9","pages":""},"PeriodicalIF":3.0,"publicationDate":"2025-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144914918","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}

引用次数: 0

Spectroscopic Study of R- and S-Ketoprofen Inclusion Complexes With 2-Hydroxypropyl-β-cyclodextrin 2-羟丙基-β-环糊精R-和s -酮洛芬包合物的光谱研究

IF 3 4区化学

Chirality Pub Date : 2025-08-12 DOI: 10.1002/chir.70045

Asma Obaid, Nujud Maslamani, Ameerah Theqah, Hind Siddiq, Reem Ghubayra, Ibtisam Mousa, Arniza Khairani Mohd Jamil, Siti Munirah Saharin, Sharifah Mohamad

{"title":"Spectroscopic Study of R- and S-Ketoprofen Inclusion Complexes With 2-Hydroxypropyl-β-cyclodextrin","authors":"Asma Obaid, Nujud Maslamani, Ameerah Theqah, Hind Siddiq, Reem Ghubayra, Ibtisam Mousa, Arniza Khairani Mohd Jamil, Siti Munirah Saharin, Sharifah Mohamad","doi":"10.1002/chir.70045","DOIUrl":"https://doi.org/10.1002/chir.70045","url":null,"abstract":"<div>\u0000 \u0000 Ketoprofen, also known as (RS)-2-(3-benzoylphenyl)-propionic acid, has the molecular formula C16H14O3 and is classified as a non-steroidal anti-inflammatory medication. R-ketoprofen has stronger analgesic effects than S-K, and as a result, there is a growing interest in enantio-recognition research, which may be accomplished through supramolecular interactions, particularly host-guest reactions. A 1:1 molar ratio was used to produce the combination of separate RK and SK and a 0.01 M stock solution of HP-β-CD to get the final concentration of 6 × 10−4 M. Ethanol was used to make stock solutions of ketoprofen enantiomers (1 mM). Researchers combined a specific volume of ketoprofen with 2-hydroxypropyl-beta-cyclodextrin (HPβ-CD) and then used spectroscopic methods to study how the S-ketoprofen (SK) and R-ketoprofen (RK) enantiomers interact with HPβ-CD to form inclusion complexes in an aqueous solution. The Benesi–Hildebrand plot was used to determine the inclusion complexes' stoichiometry ratio and binding constant; both enantiomers displayed a 1:1 stoichiometry ratio inclusion complex with HP-β-CD. Compared with SK (799 M−1), RK has a higher binding constant (1038 M−1). These results showed that HP-β-CD preferred to form inclusion complexes with RK over SK. At neutral pH, there are significant differences between RK and SK when HP-β-CD is present.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 8","pages":""},"PeriodicalIF":3.0,"publicationDate":"2025-08-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144814829","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}

引用次数: 0

Variations in the Optical Activity of L-Arginine in Electrolyte and Nonelectrolyte Solutions l -精氨酸在电解质和非电解质溶液中的旋光性变化

IF 2.8 4区化学

Chirality Pub Date : 2025-07-22 DOI: 10.1002/chir.70044

Joong-Won Shin

引用次数: 0

Chiral Separation and Molecular Simulation of Five Quinolones on a Bonded Amylose[(S)-α-Methylbenzyl Carbamate] Column (CHIRALPAK IH) and the Elucidation of Its Recognition Mechanism 5种喹诺酮类药物在直链淀粉[(S)-α-氨基甲酸甲酯]键合柱（CHIRALPAK IH）上的手性分离、分子模拟及其识别机制的阐明

IF 2.8 4区化学

Chirality Pub Date : 2025-07-17 DOI: 10.1002/chir.70050

Xiangwen Chen, Xuan Chen, Juan Pan, Shuqi Deng, Qiubing Qin, Qiang Fu, Jiliang Cao

{"title":"Chiral Separation and Molecular Simulation of Five Quinolones on a Bonded Amylose[(S)-α-Methylbenzyl Carbamate] Column (CHIRALPAK IH) and the Elucidation of Its Recognition Mechanism","authors":"Xiangwen Chen, Xuan Chen, Juan Pan, Shuqi Deng, Qiubing Qin, Qiang Fu, Jiliang Cao","doi":"10.1002/chir.70050","DOIUrl":"https://doi.org/10.1002/chir.70050","url":null,"abstract":"<div>\u0000 \u0000 In this work, the silica gel bonded amylose[(S)-α-methylbenzyl carbamate] (CHIRALPAK IH) was chosen as the chiral stationary phase (CSP) for the separation of five quinolone enantiomers by high-performance liquid chromatography (HPLC), namely, ofloxacin, flumequine, nadifloxacin, lomefloxacin, and clinafloxacin. The mobile phase composition, organic modifier, and acid–base additive were systematically investigated for the baseline separation of these five interested quinolones. The optimized mobile phases were n-hexane–ethanol–acetic acid–diethylamine (60:40:0.2:0.2, v/v/v/v) for ofloxacin and nadifloxacin, n-hexane–ethanol–acetic acid–diethylamine (60:40:0.2:0.2, v/v/v/v) for flumequine, n-hexane–isopropanol–acetic acid–diethylamine (60:40:0.3:0.3, v/v/v/v) for lomefloxacin, and n-hexane–ethanol–acetic acid–diethylamine (70:30:0.3:0.3, v/v/v/v) for clinafloxacin. The interaction forces between the amylose CSP and target quinolones were simulated by computerized molecular docking to study their enantiorecognition mechanisms. The results indicated that hydrogen bonding, π–π stacking, and hydrophobic interactions collectively contributed to the stereoselective binding. The differences in these interaction forces between the quinolone enantiomers, particularly the greater contribution of hydrogen bonding in one enantiomer compared to the other, led to a significant difference in binding energy. This differential binding energy ultimately governed the elution order and enabled chiral recognition of the five quinolone enantiomers.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 8","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144647459","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}

引用次数: 0

Chiral Post-Modification of UiO-66-NH2 on Gas Chromatography Chiral Separation UiO-66-NH2在气相色谱手性分离中的后处理

IF 2.8 4区化学

Chirality Pub Date : 2025-07-17 DOI: 10.1002/chir.70049

Jia Huang, Yizhuo Ma, Maria Abbasi, Junzhe Qin, Mingxuan Li, Zi Yang, Xuran Sun, Wei Wang, Zhen Wang, Fang Liu, Luo Aiqin, Lina Geng

{"title":"Chiral Post-Modification of UiO-66-NH2 on Gas Chromatography Chiral Separation","authors":"Jia Huang, Yizhuo Ma, Maria Abbasi, Junzhe Qin, Mingxuan Li, Zi Yang, Xuran Sun, Wei Wang, Zhen Wang, Fang Liu, Luo Aiqin, Lina Geng","doi":"10.1002/chir.70049","DOIUrl":"https://doi.org/10.1002/chir.70049","url":null,"abstract":"<div>\u0000 \u0000 As enantiomers can have different pharmacological and toxicological impacts even though they have the analogous chemical composition, efficient chiral separation is crucial. Chromatography is one of the primary methods for separating enantiomers, and the key to chromatographic separation lies in the chiral stationary phase (CSP). Chiral porous materials have emerged as innovative chiral stationary phases and garnered extensive attention. Zr based MOF materials, have been regarded as one of the most stable metal–organic framework (MOF) materials. In this paper, after grafting with L-proline, UiO-66 was used for the first time for chiral gas chromatography separation. The newly developed CSP provided high resolution for xylenes within only 2–3 min. For substances like linalool, α-pinene, and xylenes, the UiO-66-NH2-L-Pro–coated capillary column acquired bas3ic resolution and showed outstanding enantiomeric and positional isomer isolation. Comprehensive characterizations, including SEM, XRD, FT-IR, TGA, N2 adsorption–desorption isotherms, CD spectra, and XPS, were conducted to analyze the material stucture and chiral recognition mechanism. The chiral separation relies on transient diastereomeric complexes formed between L-proline and enantiomers, stabilized by hydrogen bonding, intermolecular forces, and steric constraints within UiO-66's micropores. These interactions enforce enantioselective discrimination via the pore's stereochemical filtering, enabling chiral resolution. This study is expected to provide significant value for both chromatographic chiral separation and large-scale chiral substance separation.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 8","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144647450","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}

引用次数: 0

Stokes Spectropolarimetry Applied to Measure Circular Birefringence Dispersion of Aqueous Solutions of Sugars Stokes光谱偏振法测定糖水溶液的圆双折射色散

IF 2.8 4区化学

Chirality Pub Date : 2025-07-08 DOI: 10.1002/chir.70047

Ruan Lucas Sousa Lima, Eric Santos da Silva, Paulo Trindade Araujo, Newton Martins Barbosa Neto

{"title":"Stokes Spectropolarimetry Applied to Measure Circular Birefringence Dispersion of Aqueous Solutions of Sugars","authors":"Ruan Lucas Sousa Lima, Eric Santos da Silva, Paulo Trindade Araujo, Newton Martins Barbosa Neto","doi":"10.1002/chir.70047","DOIUrl":"https://doi.org/10.1002/chir.70047","url":null,"abstract":"Circular birefringence (CB) is defined as the difference in refractive index for opposite circular polarization states and has played a crucial role in the development of stereochemistry and the concept of chirality. It manifests experimentally as optical rotatory dispersion (ORD), that is, the wavelength-dependent optical rotation of the plane of light polarization. However, most methods for probing ORD rely on analyzing transmitted light asymmetry at single wavelengths (usually the sodium D-line at 589 nm) with linear polarizers, which cannot discern between unpolarized and circularly polarized light, limiting the apparatus to analyze a single phenomenon. Here we showcase the use of Stokes spectropolarimetry (SSP), a versatile and cost-effective technique, to probe ORD of circularly birefringent materials. This technique allows complete analysis of the dispersive changes in polarization caused by anisotropic media, portraying a versatile experimental framework to study different types of optical anisotropies with a single spectropolarimeter. Here, aqueous solutions of chiral sucrose, fructose, and their mixtures are investigated. The ORD acquired verify that the optical rotation is proportional to the concentration of the chiral species and follows an inverse proportion with wavelength. As a case study, we show via SSP that ORD at 589 nm (D-line of sodium) is in good agreement with literature (+63.5° ± 1.4° mL g−1 dm−1 for sucrose and −83.7° ± 2.0° mL g−1 dm−1 for fructose).","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 7","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-07-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.70047","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144581961","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}

引用次数: 0

Electrochemiluminescent Chiral Sensor Based on Covalent Organic Frameworks for Discrimination of Phenylalanine Enantiomers 基于共价有机框架的电化学发光手性传感器识别苯丙氨酸对映体

IF 2.8 4区化学

Chirality Pub Date : 2025-07-06 DOI: 10.1002/chir.70040

Qinhua Liu, Xuan Kuang

引用次数: 0

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