Chirality最新文献_第3页

Quantification of Oseltamivir Phosphate Enantiomeric Impurity by Chiral HPLC Method With the Aid of Solvent Extraction and Phosphate Salt-Out Method 溶剂萃取-磷酸盐盐析手性高效液相色谱法测定磷酸奥司他韦对映体杂质含量

IF 2.8 4区化学

Chirality Pub Date : 2025-05-07 DOI: 10.1002/chir.70034

Torati Srinivas, K. V. N. Suresh Reddy, Challa Madhavi, M. Kiranmai Reddy

{"title":"Quantification of Oseltamivir Phosphate Enantiomeric Impurity by Chiral HPLC Method With the Aid of Solvent Extraction and Phosphate Salt-Out Method","authors":"Torati Srinivas, K. V. N. Suresh Reddy, Challa Madhavi, M. Kiranmai Reddy","doi":"10.1002/chir.70034","DOIUrl":"https://doi.org/10.1002/chir.70034","url":null,"abstract":"A robust chiral high-performance liquid chromatography (HPLC) method was established to separate and quantify the enantiomeric impurity (3S, 4S, 5R) in oseltamivir phosphate. A new sample preparation approach was used, involving the solvent extraction method to remove phosphate salt from the drug, thereby preventing the column's clogging and confirming method repeatability. Thin-layer chromatography (TLC) was employed to identify oseltamivir in the organic layer, while 31P nuclear magnetic resonance (NMR) spectroscopy and the molybdenum blue method were used to confirm the presence of phosphate in the aqueous layer. An ion-pair reversed-phase HPLC method with indirect UV detection was utilized to quantify the phosphate in both the organic and aqueous phases. Chromatographic separation of enantiomeric impurity (3S, 4S, 5R) from oseltamivir phosphate drug substances (3R, 4R, 5S) was accomplished using a Chiralpak IC-3 column with a mobile phase consisting of n-hexane, methanol, isopropyl alcohol, and diethyl amine (85:10:5:0.2, v/v/v/v) at a flow rate of 0.6 mL/min and a detection wavelength of 225 nm. The selectivity of method is clearly proved by separating the impurity from oseltamivir phosphate drug substance, with a resolution of more than 3.0. The method displayed exceptional linearity over a range of 0.035–0.300%w/w, with limits of detection of 0.005%w/w and quantification of 0.035%w/w. Consistent recovery rates were obtained between 91% and 94%, and the analytical solution remains stable for up to 72 h at 2°C–8°C.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 5","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.70034","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143919454","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

Cross-Linked Aggregates of Tyrosinase for the Efficient Synthesis of L-DOPA 酪氨酸酶交联聚集体高效合成左旋多巴

IF 2.8 4区化学

Chirality Pub Date : 2025-05-06 DOI: 10.1002/chir.70035

Dhanapal Priyadarshini, Shalini Basetty, Kunta Chandrashekar, Gurrala Sheelu, Thenkrishnan Kumaraguru

引用次数: 0

Determination of Enantiomeric Excess via 31P-NMR 用31P-NMR测定对映体过量

IF 2.8 4区化学

Chirality Pub Date : 2025-04-01 DOI: 10.1002/chir.70032

Ellis Guernsey, Jean-Luc Montchamp

{"title":"Determination of Enantiomeric Excess via 31P-NMR","authors":"Ellis Guernsey, Jean-Luc Montchamp","doi":"10.1002/chir.70032","DOIUrl":"https://doi.org/10.1002/chir.70032","url":null,"abstract":"<div>\u0000 \u0000 31P is a very attractive nucleus for nuclear magnetic resonance (NMR) analysis because of the large chemical dispersion and the simplicity of the spectra when compared with other nuclei (other than 19F). The ability to rapidly and quantitatively assay for enantiomeric excess (ee) measurements of alcohols, amines, thiols, and other chiral species using 31P-NMR is essential. Analysis of ee is particularly important in the pharmaceutical industry because a majority of medicinal compounds contain chiral centers, and enantiomers may possess different pharmacological activities. Although high-performance liquid chromatography (HPLC) with chiral stationary phase has become the standard method for ee determination, it can often be expensive and time consuming and requires purified samples. 31P-NMR offers advantages over many other nuclei as the interpretation is rapid and can have large chemical shift differences (Δδ) when comparing diastereomers. Proton decoupling avoids overlapping signals by preventing proton coupling, which could result in overlapping signals. With the rapid growth of asymmetric organocatalysis and asymmetric synthesis, the ability to quickly determine ee via phosphorus containing chiral derivatizing agents (CDAs) and chiral solvating agents (CSAs) is of utmost utility. It might be especially useful if used to determine ee directly in a reaction mixture, thereby alleviating any need for purification. This review focuses on ee determination by 31P-NMR.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 4","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143749444","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

Development of New Chiral Amino Alcohol Ligand for the Asymmetric Transfer Hydrogenation of Ketones and Its Immobilization Onto Nanomaterials for an Ease of Recovery and Reuse 新型酮类不对称转移加氢手性氨基醇配体的研制及其在纳米材料上的固定化

IF 2.8 4区化学

Chirality Pub Date : 2025-03-07 DOI: 10.1002/chir.70031

Ludovica Primitivo, Martina De Angelis, Giulia Lucci, Luciano Bonanni, Lorenza Suber, Giuliana Righi, Alessandra Ricelli

{"title":"Development of New Chiral Amino Alcohol Ligand for the Asymmetric Transfer Hydrogenation of Ketones and Its Immobilization Onto Nanomaterials for an Ease of Recovery and Reuse","authors":"Ludovica Primitivo, Martina De Angelis, Giulia Lucci, Luciano Bonanni, Lorenza Suber, Giuliana Righi, Alessandra Ricelli","doi":"10.1002/chir.70031","DOIUrl":"https://doi.org/10.1002/chir.70031","url":null,"abstract":"<div>\u0000 \u0000 This study has been carried out to extend the validation of an amino alcohol catalyst in the asymmetric transfer hydrogenation (ATH) of ketones. Previously, the catalyst was tested in asymmetric addition to several aromatic aldehydes with good to excellent results. After having optimized the reaction conditions and tested different amino residues, the best catalyst was tested in ATH of various aromatic ketones, leading to generally high yields (up to > 95%) and moderate to good enantioselectivities (ee 24%–69%). Moreover, considering the lack of examples of recoverable and reusable amino alcohol–based nanostructured catalysts for the ATH, the catalyst of choice was immobilized on proper functionalized superparamagnetic core–shell magnetite–silica nanoparticles and employed in an ATH reaction in semi-homogeneous phase. The obtained nanocatalyst exhibited a moderate catalytic efficiency in the ATH, that remains unchanged in the three catalytic cycles performed, even if noticeably worse than in the homogeneous counterpart.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 3","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143564929","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

Electrochemical Recognition of Phenylalanine Enantiomers Based on Silver Nanoparticles Modified Aminated Carbon Nanotubes 纳米银修饰胺化碳纳米管对苯丙氨酸对映体的电化学识别

IF 2.8 4区化学

Chirality Pub Date : 2025-03-06 DOI: 10.1002/chir.70029

Minfang Ji, Feiting Cao, Sha Li, Licheng Xie, Yan Jiang

{"title":"Electrochemical Recognition of Phenylalanine Enantiomers Based on Silver Nanoparticles Modified Aminated Carbon Nanotubes","authors":"Minfang Ji, Feiting Cao, Sha Li, Licheng Xie, Yan Jiang","doi":"10.1002/chir.70029","DOIUrl":"https://doi.org/10.1002/chir.70029","url":null,"abstract":"<div>\u0000 \u0000 By utilizing β-cyclodextrin (β-CD) and bovine serum albumin (BSA) as chiral selectors, a simple method was employed to fabricate an electrochemical sensor that modified with aminoized multiwall carbon nanotubes (NH2-MWCNT) and silver nanoparticles (AgNPs). The appearance and structure of the chiral sensor were characterized through X-ray powder diffraction, scanning electron microscopy, transmission electron microscope, Fourier transform infrared spectroscopy, ultraviolet–visible spectrophotometer, and X-ray photoelectron spectroscopy. The electrochemical chiral recognition behavior of the phenylalanine (Phe) enantiomer was achieved by differential pulse voltammetry. The working chiral recognition is based on the “three-point action principle.” The hydrogen bond between chiral selectors and Phe is the key to chiral recognition. Under the optimal experimental conditions, the oxidation peak current ratio of D-Phe to L-Phe (ID/IL) was 1.71. In the linear range of 3–15 mM, the detection limits of D-Phe and L-Phe are 4.62 and 5.23 μM (S/N = 3), respectively. It is noteworthy that the sensor possessed good stability and reproducibility.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 3","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143554945","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

Computational Molecular Docking Analysis of Linalool Enantiomers Interaction With Mitogen-Activated Protein Kinase 1 (MAPK1): Insights Into Potential Binding Mechanisms and Affinity 芳樟醇对映体与丝裂原活化蛋白激酶1 （MAPK1）相互作用的计算分子对接分析：对潜在结合机制和亲和力的见解

IF 2.8 4区化学

Chirality Pub Date : 2025-03-06 DOI: 10.1002/chir.70030

Halima Oulad Ali, Nasser Belboukhari, Khaled Sekkoum, Mebarka Belboukhari, Lamia Salima Seddiki

{"title":"Computational Molecular Docking Analysis of Linalool Enantiomers Interaction With Mitogen-Activated Protein Kinase 1 (MAPK1): Insights Into Potential Binding Mechanisms and Affinity","authors":"Halima Oulad Ali, Nasser Belboukhari, Khaled Sekkoum, Mebarka Belboukhari, Lamia Salima Seddiki","doi":"10.1002/chir.70030","DOIUrl":"https://doi.org/10.1002/chir.70030","url":null,"abstract":"<div>\u0000 \u0000 Molecular docking analysis of linalool interaction with mitogen-activated protein kinase 1 (MAPK1) provides valuable insights into the potential binding mechanisms and affinity of this interaction. Linalool, a naturally occurring terpene alcohol, has been the subject of increasing interest due to its diverse pharmacological properties, including anti-inflammatory, antioxidant, and anticancer activities. MAPK1 is a crucial signaling protein involved in various cellular processes, including cell proliferation, differentiation, and survival. Using MOE software, we conducted a stereoisomer analysis of (R)- and (S)-linalool in our study. After docking, the ligand was ranked according to their binding energy and the best lead compound was selected based on the highest binding energy. The results showed that the S-linalool isomer showed superior anticancer activity, while the R-linalool molecule showed less activity. This interaction could provide insights into linalool's potential therapeutic applications, highlighting its diverse pharmacological properties.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 3","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143554929","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

Exploring Naproxen Cocrystals Through Solid-State Vibrational Circular Dichroism 通过固态振动圆二色性探索萘普生共晶

IF 2.8 4区化学

Chirality Pub Date : 2025-02-17 DOI: 10.1002/chir.70027

Adam Sklenář, Anne Zehnacker-Rentien, Jakub Kaminský, Jan Rohlíček, Petr Bouř

{"title":"Exploring Naproxen Cocrystals Through Solid-State Vibrational Circular Dichroism","authors":"Adam Sklenář, Anne Zehnacker-Rentien, Jakub Kaminský, Jan Rohlíček, Petr Bouř","doi":"10.1002/chir.70027","DOIUrl":"https://doi.org/10.1002/chir.70027","url":null,"abstract":"Vibrational circular dichroism (VCD) spectroscopy appears as a useful method for characterizing optically active substances in the solid state. This is particularly important for active pharmaceutical ingredients. However, measurement and interpretation of the spectra bring about many difficulties. To assess the experimental and computational methodologies, we explore an anti-inflammatory drug, naproxen. Infrared (IR) and VCD spectra of the pure compound and its cocrystals with alanine and proline were recorded, and the data were interpreted by quantum chemical simulations based on a cluster model and density functional theory. Although unpolarized IR spectroscopy can already distinguish pure ingredients from cocrystals or a mixture, the VCD technique is much more sensitive. For example, the naproxen carboxyl group strongly interacts with the zwitterionic alanine in the cocrystal via two strong hydrogen bonds, which results in a rather rigid structure crystallizing in the chiral P212121 Sohncke group and its VCD is relatively strong. In contrast, the d-proline and (S)-naproxen cocrystal (P21 group) involves a single hydrogen bond between the subunits, which together with a limited motion of the proline ring gives a weaker signal. Solid-state VCD spectroscopy thus appears useful for exploring composite crystal structures and interactions within them, including studies of pharmaceutical compounds.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 3","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.70027","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143431509","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

A Novel, Simple, Isocratic HPLC-UV Method for Determination of Chiral Purity for Dibenzoyl-L-Tartaric Acid (L-DBTA) 一种新型、简便、等密度HPLC-UV法测定二苯甲酰- l-酒石酸（L-DBTA）手性纯度

IF 2.8 4区化学

Chirality Pub Date : 2025-02-17 DOI: 10.1002/chir.70028

Pradeep Kumar Gollapudi, Padmaja Nimmagadda, Kranthi Kumar Gollapudi

{"title":"A Novel, Simple, Isocratic HPLC-UV Method for Determination of Chiral Purity for Dibenzoyl-L-Tartaric Acid (L-DBTA)","authors":"Pradeep Kumar Gollapudi, Padmaja Nimmagadda, Kranthi Kumar Gollapudi","doi":"10.1002/chir.70028","DOIUrl":"https://doi.org/10.1002/chir.70028","url":null,"abstract":"<div>\u0000 \u0000 Dibenzoyl-L-tartaric acid (L-DBTA) is a crucial compound in the synthesis of chiral molecules, particularly within the pharmaceutical industry. Ensuring the enantiomeric purity of L-DBTA is essential for regulatory compliance, quality control, and process optimization. To achieve this, a high-performance liquid chromatography (HPLC) method was developed and validated for determining the D-DBTA content in L-DBTA. The method validation adhered to ICH Q2(R2) guidelines, covering parameters such as system suitability, solution stability, robustness, linearity, range, limit of detection (LOD), limit of quantification (LOQ), accuracy, and precision. HPLC separation was performed using a Chiral PAK IA column (250 × 4.6 mm, 5.0 μm) with an isocratic mobile phase consisting of n-heptane, isopropanol (IPA), and trifluoroacetic acid (900:100:1 v/v/v). The column temperature was maintained at 40°C, and the sample cooler was kept at ambient conditions. Detection was carried out at 230 nm, achieving a resolution greater than 1.5 between L-DBTA and D-DBTA. The method demonstrated excellent linearity over a range of 30%–200% of the specification limit, with accuracy and range established from the LOQ level to 200%. Solution stability was confirmed for 1 day at room temperature, and precision was validated at both the LOQ and 100% levels. All validation parameters met the acceptance criteria, confirming the method's suitability for routine testing and batch release at quality control sites. This HPLC method is both sensitive and selective, ensuring the reliable determination of chiral purity in L-DBTA and its impurities.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 3","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143423817","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

Development of Acid-Functionalized Molecularly Imprinted Phenolic Resin for Chiral Recognition of S-Venlafaxine 用于手性识别s -文拉法辛的酸功能化分子印迹酚醛树脂的研制

IF 2.8 4区化学

Chirality Pub Date : 2025-02-17 DOI: 10.1002/chir.70023

Rua B. Alnoman

{"title":"Development of Acid-Functionalized Molecularly Imprinted Phenolic Resin for Chiral Recognition of S-Venlafaxine","authors":"Rua B. Alnoman","doi":"10.1002/chir.70023","DOIUrl":"https://doi.org/10.1002/chir.70023","url":null,"abstract":"<div>\u0000 \u0000 This article reports the synthesis of a molecularly imprinted phenolic formaldehyde resin for the selective recognition of the cationic S-enantiomer of venlafaxine. The resin was developed through the condensation polymerization of p-hydroxybenzoic acid (4-HBA) and 4-nitrophenol (4-NP) with formaldehyde in an acidic medium. The resultant polymer was reduced to introduce amino groups into the polymer to obtain a dual-functional resin with amino and carboxylic groups (CA-P). After the uptake of S-VF, glutaraldehyde cross-linking stabilized the resin and formed its enantioselective cavities. Adsorption studies showed that optimum conditions occurred at pH 7, whereas the maximum adsorption capacity was 420 mg/g according to the Langmuir isotherm. The selectivity coefficient of S-VF-IP was 13 times that of NIP, confirming that the imprinting process indeed occurred. Chiral separation experiments using the SV-imprinted polymer (S-VF-IP) column resulted in 98% enantiomeric excess for R-VF, whereas the respective NIP did not provide any enantioselectivity. These results show a great possibility of the developed resin in efficient enantioselective separation and offer a promising method for the purification of chiral drugs from racemic mixtures in pharmaceutical applications.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 3","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143431510","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

On the (Im)possible Interplays Between Natural and Magnetic Optical Activity in Chiral Samples 手性样品中自然光学活性与磁光学活性之间可能的相互作用

IF 2.8 4区化学

Chirality Pub Date : 2025-02-13 DOI: 10.1002/chir.70024

Francesco Zinna

引用次数: 0