Chirality最新文献_第2页

Enantiodifferentiation of Thiohydantoin Derivatives by NMR in the Presence of Chiral Solvating Agent: (1R,2S)-Ephedrine and Chiral Symmetrical and Unsymmetrical Thioureas

IF 2.8 4区化学

Chirality Pub Date : 2025-01-23 DOI: 10.1002/chir.70013

Sevgi Sarigul Ozbek, Senel Teke Tuncel, Sule Erol Gunal, Ilknur Dogan

{"title":"Enantiodifferentiation of Thiohydantoin Derivatives by NMR in the Presence of Chiral Solvating Agent: (1R,2S)-Ephedrine and Chiral Symmetrical and Unsymmetrical Thioureas","authors":"Sevgi Sarigul Ozbek, Senel Teke Tuncel, Sule Erol Gunal, Ilknur Dogan","doi":"10.1002/chir.70013","DOIUrl":"10.1002/chir.70013","url":null,"abstract":"<div>\u0000 \u0000 2-Thiohydantoin derivatives, including different substitutions at N-1 and C-5 (5-methyl-, 5-isopropyl-, 1-acetyl-5-methyl-, and 1-acetyl-5-isopropyl-) (1–4, respectively), were synthesized by the known literature methods. In these synthetic pathways, it was reported that enantiomerically pure 2-thiohydantions were obtained in the absence of any solvent via the reaction of L-amino acids with thiourea (1&2) and via the reaction of L-amino acids with NH4SCN and acetic anhydride (3&4). However, in this study, in contrary to the previous literature studies, racemic mixtures of 2-thiohydantoins were obtained although the same synthetic methods were used. The racemic nature of 2-thiohydantoin derivatives (1–4) was proved by using 1H NMR analysis in the presence of (1R,2S)-(−)-ephedrine as a chiral auxiliary. In addition, the enantiomers of 3&4 were also resolved on chiral stationary phases by HPLC analyses. Furthermore, newly synthesized unsymmetrical chiral thioureas (S-1&S-2) and previously synthesized symmetrical ones (SS-3&SS-4) were used as chiral solvating agent (CSA) for the enantiodiscrimination of the thiohydantoins (5&6), previously reported. Optimal CSA/substrate ratios were determined for the best enantiodiscrimination.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 2","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143021639","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

Optimizing Enantiomeric Resolution of Chiral Triazoles in Supercritical Fluid Chromatography

IF 2.8 4区化学

Chirality Pub Date : 2025-01-23 DOI: 10.1002/chir.70016

Codruţa Frîncul, Alina Ghinet, Dalila Belei, Bezhan Chankvetadze, Sergiu Shova, Emmanuelle Lipka, Anca-Elena Dascălu

引用次数: 0

Controlling Sign and Magnitude of Circularly Polarized Luminescence of Axially Chiral Schiff-Base Boron Difluoride Complexes Bearing Polyethylene Glycol Chains 含聚乙二醇链的轴向手性席夫碱二氟化硼配合物圆偏振发光的控制符号和大小。

IF 2.8 4区化学

Chirality Pub Date : 2025-01-14 DOI: 10.1002/chir.70014

Masahiro Ikeshita, Miku Ichinose, Daiya Suzuki, Jungo Ono, Yoshitane Imai, Takashi Tsuno

引用次数: 0

Proceedings From 19th International Conference on Chiroptical Spectroscopy, Hiroshima, Japan 第十九届国际光谱学会议论文集，日本广岛。

IF 2.8 4区化学

Chirality Pub Date : 2025-01-14 DOI: 10.1002/chir.70015

Koichi Matsuo, Tatsuo Nehira, Nina Berova, Gennaro Pescitelli, Oliver Trapp, Simona Collina

引用次数: 0

Construction of a Vibrational Circular Dichroism Instrument Equipped With a Thermoelectrically Cooled Detector for Prolonged Measurements 带热电冷却探测器的振动圆二色仪的研制。

IF 2.8 4区化学

Chirality Pub Date : 2025-01-14 DOI: 10.1002/chir.70019

Hisako Sato, Masaru Shimizu, Keisuke Watanabe, Jun Koshoubu

引用次数: 0

Enantioselective Degradation and Processing Factors of Seven Chiral Pesticides During the Processing of Wine and Rice Wine 7种手性农药在酒和黄酒加工过程中的对映选择性降解及加工因素

IF 2.8 4区化学

Chirality Pub Date : 2025-01-12 DOI: 10.1002/chir.70018

Yuting Tan, Nuanhui Wen, Zhiqiang Lu, Wenjie Wei, Haiyan Shi, Minghua Wang

{"title":"Enantioselective Degradation and Processing Factors of Seven Chiral Pesticides During the Processing of Wine and Rice Wine","authors":"Yuting Tan, Nuanhui Wen, Zhiqiang Lu, Wenjie Wei, Haiyan Shi, Minghua Wang","doi":"10.1002/chir.70018","DOIUrl":"10.1002/chir.70018","url":null,"abstract":"<div>\u0000 \u0000 Chiral pesticides often undergo enantioselective degradation during food fermentation. In this study, the enantioselective fates of seven chiral pesticides during processing of wine and rice wine were investigated. The results revealed that R-metalaxyl, R-mefentrifluconazole and S-hexaconazole were preferentially degraded during wine processing with EF values of 0.57, 0.78, and 0.43, respectively, whereas S-metalaxyl and R-hexaconazole were preferentially degraded during rice wine processing with EF values of 0.44 and 0.54, respectively. Stereoselectivity was attributed to fermentative bacterial activity. The processing factor (PF) values for the five pesticides ranged from 0.04 to 0.34 during wine processing and from 0.02 to 0.29 during rice wine processing, suggesting that fermentation can mitigate pesticide exposure risks and ensure food safety. This study enhances our understanding of enantioselective fate of chiral pesticides during fermented food processing, provides guidance for the application of chiral pesticides, and enables the dietary risk of chiral pesticides in processed products to be assessed more accurately.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142969866","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

Novel Approach for Efficient Separation of Primary Amines Using Supercritical Fluid Chromatography 超临界流体色谱法高效分离伯胺的新方法

IF 2.8 4区化学

Chirality Pub Date : 2025-01-12 DOI: 10.1002/chir.70012

Binhao Wang, Yu Shen, Ruonan Hao, Shuheng Pan, Ruizhi Han, Ye Ni

{"title":"Novel Approach for Efficient Separation of Primary Amines Using Supercritical Fluid Chromatography","authors":"Binhao Wang, Yu Shen, Ruonan Hao, Shuheng Pan, Ruizhi Han, Ye Ni","doi":"10.1002/chir.70012","DOIUrl":"10.1002/chir.70012","url":null,"abstract":"<div>\u0000 \u0000 Efficient enantioselective separation is a critical process in pharmaceutical and chemical industries for the production of chiral compounds. Herein, we developed a novel approach for the efficient enantioselective separation of primary amines using supercritical fluid chromatography (SFC) with a commercially available SFC column, Cel1. The key factors of separation, including cosolvent ratios, total cosolvent percentages, and temperature, were systematically assessed in this study. It revealed that utilization of a cosolvent mixture consisting of methanol and isopropanol in a 1:3 (v/v) ratio with a low total cosolvent percentage of 5% resulted in superior retention and selectivity. Additionally, it was observed that maintaining mid-range temperatures at 30 and 35°C achieved optimal balance between retention and efficiency. Employment of commercially available SFC columns streamlined the separation process, reducing analysis time and labor. This study highlights the effectiveness of SFC as a powerful tool for conducting high-throughput enantioselective separations in pharmaceutical and fine chemical industries.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142969868","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

Enantioselective Analysis and Separation of Two β-Blockers via Derivatization Approach 衍生化法分离两种β受体阻滞剂的对映选择性分析。

IF 2.8 4区化学

Chirality Pub Date : 2025-01-06 DOI: 10.1002/chir.70010

Vinod, Shubham Sharma, Rajasekhar V. S. R. Pullabhotla, Ankit Mittal

{"title":"Enantioselective Analysis and Separation of Two β-Blockers via Derivatization Approach","authors":"Vinod, Shubham Sharma, Rajasekhar V. S. R. Pullabhotla, Ankit Mittal","doi":"10.1002/chir.70010","DOIUrl":"10.1002/chir.70010","url":null,"abstract":"<div>\u0000 \u0000 Enantiomeric analysis of chiral drugs is very significant, as their enantiomers display different pharmacological or toxicological behavior towards living systems. Among these drugs, β-blockers are available as racemates, where their enantiomers display different pharmacological effects. Herein, we report enantioselective separation of two β-blockers, namely, atenolol and sotalol, using a derivatization approach. The analytes were derivatized with “(S)-1-[1H-benzo(d)(1,2,3)triazol-1-yl]-2-[6-methoxynaphthalen-2-yl-propan-1-one]” {(S)-BTMNP} in a straightforward derivatization step. The resulting diastereomers were separated on a reverse-phase HPLC C18 column with a mobile phase composed of acetonitrile and TEAP buffer (75:25, v/v, pH = 3.5) and detection at 230 nm. This method achieved successful enantiomer separation for both drugs within 20 min, yielding resolution values greater than 3.8. The detection limits were determined to be 6.4 and 4.6 ng mL−1 for atenolol and sotalol, respectively, which indicated sensitivity and effectiveness of the method for the analysis of two β-blockers from their dosage formulations.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-01-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142930699","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

A Chiral Porous Organic Polymer Used as the Stationary Phase for High-Resolution Gas Chromatography Separations 一种用作高分辨率气相色谱分离固定相的手性多孔有机聚合物。

IF 2.8 4区化学

Chirality Pub Date : 2025-01-06 DOI: 10.1002/chir.70011

Wei Wang, Zhen Wang, Yuwei Wang, Liquan Sun, Jiangjiang Zhang, Yukui Zhang, Aiqin Luo

{"title":"A Chiral Porous Organic Polymer Used as the Stationary Phase for High-Resolution Gas Chromatography Separations","authors":"Wei Wang, Zhen Wang, Yuwei Wang, Liquan Sun, Jiangjiang Zhang, Yukui Zhang, Aiqin Luo","doi":"10.1002/chir.70011","DOIUrl":"10.1002/chir.70011","url":null,"abstract":"<div>\u0000 \u0000 A chiral porous organic polymer (cPOP) was synthesized through nucleophilic substitution polymerization between dichloromaleimide and aromatic amine. This cPOP was used as a new chiral stationary phase (CSP) for gas chromatography (GC) chiral separation. In this work, we first used this cPOP as the CSP for gas chromatography to investigate its ability to separate racemic mixtures, including amino acid derivatives, chiral alcohols, aldehydes, alkanes, ketones, esters, and organic acids. The results showed that the column can effectively separate various racemic mixtures and achieve baseline separation of threonine (Rs = 1.91). Furthermore, the separation mechanism was elucidated by density functional theory (DFT) simulation. Additionally, the cPOP column demonstrated good repeatability and stability. The relative standard deviations (RSDs) for intraday were 0.11%–0.12% (n = 3) for the retention time of n-butyl glycidyl ether, 0.1%–0.34% (n = 3) for interday, and 2.25%–3.37% (n = 3) for column to column. This work shows that cPOP has good potential as chiral stationary phases in gas chromatography.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-01-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142930653","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

Enantio-Recognition and Charge Transfer Complex Formation Involving Tetrathiafulvalene-Appended Chiral 1,2-Cyclohexane-Diamine: An Integrated Experimental and Theoretical Study 含四硫丁烯-附手性1,2-环己烷-二胺的对映体识别和电荷转移络合物的形成：实验和理论的综合研究。

IF 2.8 4区化学

Chirality Pub Date : 2024-12-18 DOI: 10.1002/chir.70009

Camilla Ferrari, Alexandra Bogdan, Flavia Pop, Cosimo Curto, Alberta Carella, Francesco Rossella, Narcis Avarvari, Claudio Fontanesi

{"title":"Enantio-Recognition and Charge Transfer Complex Formation Involving Tetrathiafulvalene-Appended Chiral 1,2-Cyclohexane-Diamine: An Integrated Experimental and Theoretical Study","authors":"Camilla Ferrari, Alexandra Bogdan, Flavia Pop, Cosimo Curto, Alberta Carella, Francesco Rossella, Narcis Avarvari, Claudio Fontanesi","doi":"10.1002/chir.70009","DOIUrl":"10.1002/chir.70009","url":null,"abstract":"In this work, we exploit the electronic features of tetrathiafulvalene (TTF) as a backbone in synthesizing chiral derivatives. The aim is to make use of TTF's well-known and unique redox and semiconducting properties in the fields of enantio-selective recognition and chiral charge transfer (CT) complex preparation, with the ultimate objective of obtaining devices with various potential applications, ranging from plasmonics to quantum computing. In particular, both cyclohexane-bis (TTF-amide)–based enantiomers 1-(S,S) and 1-(R,R), stable under an oxidation regime, have been selected, and under these conditions, the electrochemical enantiospecific response of the four possible systems, coming from the combination with L- and D-tartaric acid, respectively, was tested. The 1:tartaric acid adducts show lower oxidation potentials than the pristine 1, together with clear enantio-discrimination demonstrated by sizeable potential differences in the range of 29–46 mV between the diastereomeric adducts. Because the oxidation potential of 1 suggests the possibility of the formation of CT complexes, impedance and FT-IR spectra were recorded to confirm this hypothesis in the case of the CT complex 1:I2. The experimental results obtained through the FT-IR analysis were also compared with the theoretical results deriving from the DFT-based calculations.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.70009","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142852948","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