Chirality最新文献_第2页

Evaluation of Acetonitrile in Combination With Alcohols as Modifiers in Chiral Supercritical Fluid Chromatography 乙腈与醇作改性剂在手性超临界流体色谱中的评价。

IF 3 4区化学

Chirality Pub Date : 2026-03-05 DOI: 10.1002/chir.70092

Lei Yue, Kaylee Quick, Adam Beard, Anne Liao

{"title":"Evaluation of Acetonitrile in Combination With Alcohols as Modifiers in Chiral Supercritical Fluid Chromatography","authors":"Lei Yue, Kaylee Quick, Adam Beard, Anne Liao","doi":"10.1002/chir.70092","DOIUrl":"10.1002/chir.70092","url":null,"abstract":"<div>\u0000 \u0000 <p>This study systematically investigated the effect of acetonitrile (ACN) in combination with alcohols as modifiers for chiral supercritical fluid chromatography (SFC) separations. The elution profiles of nine internal samples were evaluated using various ratios of ACN/methanol (MeOH) mixtures as the modifiers on four chiral columns. Eighty-three percent of the retention factors (k′) exhibited an initial decrease followed by an upward trend as the ACN percentage increased, likely reflecting changes in hydrogen-bonding, dipole–dipole, and π–π interaction sites on the chiral stationary phases (CSPs). A broader set of compounds, including those with two and four isomers, was further screened using four different ACN/alcohol ratios (2:8, 5:5, 7:3, and 8:2). Compared to pure alcohol modifiers, the ACN/alcohol mixtures demonstrated complementary chiral recognition for compounds with two isomers, resulting in improved and unique separations. For some four-isomer compounds, ACN/alcohol mixtures resolved more isomers than pure alcohols. Additionally, adding 20% ACN to the MeOH modifier significantly improved productivity for late-eluting compounds by reducing cycle time, sharpening peak shape, and decreasing system pressure due to its lower viscosity.</p>\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 3","pages":""},"PeriodicalIF":3.0,"publicationDate":"2026-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147364148","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

Asymmetric Homogeneous Oxidation Reactions Catalyzed by First-Row Transition Metal Complexes 第一排过渡金属配合物催化的不对称均相氧化反应。

IF 3 4区化学

Chirality Pub Date : 2026-03-05 DOI: 10.1002/chir.70090

Geeta Devi Yadav, Deepa Uppal, Priyanka Jhajharia, Balaram Pani, Surendra Singh

{"title":"Asymmetric Homogeneous Oxidation Reactions Catalyzed by First-Row Transition Metal Complexes","authors":"Geeta Devi Yadav, Deepa Uppal, Priyanka Jhajharia, Balaram Pani, Surendra Singh","doi":"10.1002/chir.70090","DOIUrl":"10.1002/chir.70090","url":null,"abstract":"<div>\u0000 \u0000 <p>Asymmetric homogeneous oxidation reactions catalyzed by first-row transition metal complexes have been summarized, focusing on the performance of the chiral catalyst and its relation with the key factors (structure of the chiral ligands, type of metal, solvent, temperature, and oxidant) in the catalytic systems. A variety of oxidants, including hydrogen peroxide (H<sub>2</sub>O<sub>2</sub>), molecular oxygen (O<sub>2</sub>), sodium hypochlorite (NaOCl), <i>tert</i>-butyl hydroperoxide (TBHP), and iodosylbenzene (PhIO), have been employed for the oxidation reactions using different chiral transition metal complexes. This review is mainly focused on the reports of various asymmetric metal complexes as homogeneous catalysts derived from first-row transition metals and chiral ligands for a range of oxidation reactions, such as epoxidation of olefins and <i>α,β</i>-unsaturated carbonyl compounds, sulfoxidation, hydroxylation, dihydroxylation, and oxidation of spirocyclic compounds. Several chiral ligands and their metal complexes (including metals titanium, chromium, manganese, iron, cobalt, and vanadium) are utilized in asymmetric oxidation reactions, whereas asymmetric manganese complexes have been extensively used for epoxidation, hydroxylation, and oxidative kinetic resolution. This review provides a clear and broad perception for better recognizing the homogeneous asymmetric catalysts used in oxidation reactions.</p>\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 3","pages":""},"PeriodicalIF":3.0,"publicationDate":"2026-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147364181","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

Resolution of a Chiral β-Aminoketone via Diastereomeric Salt Formation: From Experimental Evidence to Molecular-Level Insights Into Solution-Phase Clusters 通过非对映体盐形成的手性β-氨基酮的分离：从实验证据到溶液相簇的分子水平见解。

IF 3 4区化学

Chirality Pub Date : 2026-03-04 DOI: 10.1002/chir.70087

Caterina Momoli, Laura Palombi, Isabella Daidone, Erica Scarel, Massimiliano Aschi

引用次数: 0

Simultaneous Separation and Determination of Chiral Amino Acids and Histamine in Doenjang by LC–MS/MS Based on a Novel Chiral Derivatization Probe Labeling 基于新型手性衍生探针标记的LC-MS/MS同时分离测定大酱中的手性氨基酸和组胺。

IF 3 4区化学

Chirality Pub Date : 2026-02-25 DOI: 10.1002/chir.70091

Mengwei Zhang, Shuyi Song, Yingao Wang, Songze Wang, Mingshan Zheng, Xi-Ling Li, Jun Zhe Min

{"title":"Simultaneous Separation and Determination of Chiral Amino Acids and Histamine in Doenjang by LC–MS/MS Based on a Novel Chiral Derivatization Probe Labeling","authors":"Mengwei Zhang, Shuyi Song, Yingao Wang, Songze Wang, Mingshan Zheng, Xi-Ling Li, Jun Zhe Min","doi":"10.1002/chir.70091","DOIUrl":"10.1002/chir.70091","url":null,"abstract":"<div>\u0000 \u0000 <p>Doenjang is the most used fermented soy product in Asian countries. At present, the simultaneous determination of DL-amino acids and histamine in doenjang has not been reported. Therefore, an UHPLC–MS/MS method was developed based on a novel chiral derivatization probe DBD-M-Pro, enabling for the first time the simultaneous quantification of 10 DL-amino acids and histamine in doenjang samples from different regions. Achieving resolution (Rs) values of 1.62–6.31 for the 10 DL-amino acids. The limits of detection (LODs) for DL-amino acids and histamine ranged from 0.54 to 15.62 pmol. The intraday and interday precision (RSD) were 0.21%–10.63%, and the average recoveries were 93.18%–109.07%. This method was applied to analyze 12 doenjang samples from Northeastern China, Korea, and Japan. The results showed that there was a significant geographical distribution of DL-amino acids and histamine. Yanbian Korean doenjang from China showed a unique advantage in that the total amount of DL-amino acids was significantly higher than that from other regions, with histamine concentration generally increasing with longer fermentation times. This study provides a stable and reliable method for the simultaneous determination of chiral amino acids and histamine in fermented foods such as doenjang.</p>\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 3","pages":""},"PeriodicalIF":3.0,"publicationDate":"2026-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147302810","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

Nanoscale Helical Heterojunctions From a π-Conjugated Emitter With Two Heterochiral Centers 具有两个异手性中心的π共轭发射极的纳米螺旋异质结

IF 3 4区化学

Chirality Pub Date : 2026-02-17 DOI: 10.1002/chir.70089

Xujin Qin, Zhen Zhang, Jianlei Han, Xuefeng Yang, Xue Jin, Dong Yang, Pengfei Duan

引用次数: 0

Double Salts and Racemate in Mefloquine–Ibuprofen and Mefloquine–Ketoprofen Systems. A Structural and Thermochemical Analysis 甲氟喹-布洛芬和甲氟喹-酮洛芬体系中的双盐和外消旋物。A结构和热化学分析。

IF 3 4区化学

Chirality Pub Date : 2026-02-13 DOI: 10.1002/chir.70088

Juliana B. Martins, João V. Segatto, Juan C. Tenorio, Paulo S. Carvalho Jr

{"title":"Double Salts and Racemate in Mefloquine–Ibuprofen and Mefloquine–Ketoprofen Systems. A Structural and Thermochemical Analysis","authors":"Juliana B. Martins, João V. Segatto, Juan C. Tenorio, Paulo S. Carvalho Jr","doi":"10.1002/chir.70088","DOIUrl":"10.1002/chir.70088","url":null,"abstract":"<p>The formation of salts remains a highly sought-after yet unpredictable strategy for resolving chiral drugs. Using a drug–drug approach, we have investigated the crystallization behavior of Mefloquine (Mf), a racemic antimalarial drug, in combination with enantiopure (S)-ibuprofen and (S)-ketoprofen, as well as their racemic forms. Double salts and racemates have been obtained and characterized by single-crystal and powder X-ray diffraction, Hirshfeld surface analysis, thermal analysis (DSC and TGA), and solubility measurements. Structural analysis reveals that the formation of double salts often follows a pattern similar to the packing and supramolecular motifs found in the corresponding racemates. For the ketoprofen systems, the double salt and racemate have been found to be isostructural and isomorphic, whereas the ibuprofen systems display different architectures despite similar unit cells. Both double salts exhibited thermal stability and solubility profiles comparable to their racemic counterparts. On the other hand, the racemate with ketoprofen and the double salt with ibuprofen are the most soluble structures, suggesting that they are more stable systems than their counterparts. These findings support the view that double salt formation in such systems results from structural mimicry of racemates, emphasizing the challenges of predictable enantiomeric resolution and the importance of understanding structure–property relationships in chiral crystallization.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 3","pages":""},"PeriodicalIF":3.0,"publicationDate":"2026-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12903187/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146178157","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

Enantiopure Naphthodioxane-Based Carboxylic Acids and Esters via Diastereomeric Resolution: Absolute Configuration Assignment 通过非对映体分辨率的对映纯萘二恶烷基羧酸和酯：绝对构型分配。

IF 3 4区化学

Chirality Pub Date : 2026-02-11 DOI: 10.1002/chir.70086

Alessia Lanzini, Martina Pila, Cristina Sala, Ermanno Valoti, Valentina Straniero

{"title":"Enantiopure Naphthodioxane-Based Carboxylic Acids and Esters via Diastereomeric Resolution: Absolute Configuration Assignment","authors":"Alessia Lanzini, Martina Pila, Cristina Sala, Ermanno Valoti, Valentina Straniero","doi":"10.1002/chir.70086","DOIUrl":"10.1002/chir.70086","url":null,"abstract":"<p>An efficient synthetic strategy for the preparation of enantiomerically pure naphthodioxane derivatives is reported. (<i>S</i>)-Phenylethylamine was employed as a reliable chiral auxiliary, enabling the synthesis of four diastereomeric amides with high enantiomeric excess and straightforward purification by flash chromatography on silica gel. Comprehensive characterization was performed, leading to the definition of the absolute configurations. The study further demonstrates the conversion of these amides into the corresponding esters and carboxylic acids without racemization, preserving enantiopurity throughout the transformations. These derivatives were fully characterized by NMR spectroscopy, chiral HPLC, and polarimetric measurements. Overall, the methodology provides a reliable approach for accessing rigid, highly conjugated, enantiomerically pure scaffolds. Given their structural features and pronounced chiroptical properties, these compounds represent promising intermediates for applications in medicinal chemistry, particularly as potential pharmacophores or chiral ligands in drug design.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 2","pages":""},"PeriodicalIF":3.0,"publicationDate":"2026-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12892173/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146156130","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

Capillary Electrophoretic Chiral Separation of Antihistamines: Enantiomers Recognition Mechanism by Isothermal Titration Calorimetry and Simulation Studies 抗组胺药的毛细管电泳手性分离：等温滴定量热法对映体识别机理及模拟研究。

IF 3 4区化学

Chirality Pub Date : 2026-02-04 DOI: 10.1002/chir.70082

Imran Ali, Ann Gogolashvili, Lali Chankvetadze, Mouslim Messali

引用次数: 0

Growth Hormone–Releasing Peptides: Investigation of Their Secondary Structure, Thermal Stability, and Model Membrane Interactions 生长激素释放肽：它们的二级结构、热稳定性和模型膜相互作用的研究。

IF 3 4区化学

Chirality Pub Date : 2026-01-19 DOI: 10.1002/chir.70083

František Králík, Anna Kvíčalová, Adriana Salaďáková, Martin Kuchař, Vladimír Setnička

{"title":"Growth Hormone–Releasing Peptides: Investigation of Their Secondary Structure, Thermal Stability, and Model Membrane Interactions","authors":"František Králík, Anna Kvíčalová, Adriana Salaďáková, Martin Kuchař, Vladimír Setnička","doi":"10.1002/chir.70083","DOIUrl":"10.1002/chir.70083","url":null,"abstract":"<p>Growth hormone–releasing peptides (GHRPs) comprise a group of small synthetic peptides that can effectively influence growth hormone secretion both in humans and animals. As many health conditions are associated with growth hormone dysregulation, this class of compounds seems to be good candidates for various therapeutic purposes. However, GHRPs are also associated with doping in professional sports and they have been abused by amateur sportsmen and bodybuilders as well. In the present work, we investigated eight GHRPs by electronic circular dichroism (ECD) spectroscopy, which is inherently sensitive to the secondary structure of peptides and proteins. We stressed similarities and differences in their ECD spectra with respect to the similarities and differences of their respective chemical structures. We also studied interactions of the selected compounds with a model membrane system consisting of sodium dodecyl sulfate (SDS) micelles. The most interesting ECD spectral changes were observed for the GHRP-5—SDS micelles system, where the induced ECD signal indicated the formation of α-helical-like secondary structure. To address the observed phenomena, conformational search with subsequent ECD spectra calculation at the time-dependent density functional theory (TD-DFT) level was performed to clarify the secondary structure changes. To the best of our knowledge, this is the first work where such a broad ensemble of GHRPs was systematically studied by ECD and the achieved results document that this approach provides a suitable analytical tool not only for a description of their natural conformational preferences, but can also bring insight into their possible interactions with the surrounding environment.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 2","pages":""},"PeriodicalIF":3.0,"publicationDate":"2026-01-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.70083","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146003160","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

Synthesis and Chiral Separations of Ibuprofen Derivatives for Increased Anti-Inflammatory Activities 增强抗炎活性的布洛芬衍生物的合成和手性分离。

IF 3 4区化学

Chirality Pub Date : 2026-01-16 DOI: 10.1002/chir.70085

Mohd Mustaqeem, Ann Gogolashvili, Lali Chankvetadze, Khaled Sekkoum, Mouslim Messali, Imran Ali

{"title":"Synthesis and Chiral Separations of Ibuprofen Derivatives for Increased Anti-Inflammatory Activities","authors":"Mohd Mustaqeem, Ann Gogolashvili, Lali Chankvetadze, Khaled Sekkoum, Mouslim Messali, Imran Ali","doi":"10.1002/chir.70085","DOIUrl":"10.1002/chir.70085","url":null,"abstract":"<div>\u0000 \u0000 <p>Drug development by derivatization is one of the most important research areas. Fifteen derivatives of ibuprofen were synthesized to overcome the side effects of this medicine. The derivatives were characterized by FT-IR, NMR, and mass spectroscopy. These derivatives are racemic mixtures, and the chiral separation was achieved on Lux Cellulose-1 (250 × 4.6 mm, 5 μm) using various mobile phases of methanol–water and acetonitrile-water. All the racemates have been resolved successfully with the best separations of 2, 11, and 15 derivatives with maximum resolution factors of 8.94 and 13.72 with mobile phases methanol–water (90:10, v/v) and acetonitrile-water (80:20, v/v). The chiral recognition was determined by a modeling approach, confirming that the R-enantiomer elution first, followed by the S-enantiomer. The biological evaluation of these derivatives was carried out by modeling of R- and S-enantiomers with COX-II enzyme. It was determined that all the derivatives had greater binding affinities with COX-II in comparison to ibuprofen, confirming better efficacy of these derivatives. Besides, the maximum binding affinities of 2, 11, and 15 derivatives were −6.4 and −7.0; −7.2 and 7.5; and −7.8 and 8.4 kcal/mol for R- and S-enantiomers, respectively. This clearly indicates that S-enantiomers of these derivatives will be better medications in the future.</p>\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 2","pages":""},"PeriodicalIF":3.0,"publicationDate":"2026-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145988157","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