Chirality最新文献_第9页

Enantioselective polar-organic mode high-performance liquid chromatographic separation of lifitegrast on immobilized polysaccharide stationary phase and its application to pH-dependent chiral interconversion studies 固定化多糖固定相上对立面选择性极性-有机模式高效液相色谱分离利菲格拉司特及其在 pH 依赖性手性相互转化研究中的应用

IF 2 4区化学

Chirality Pub Date : 2024-01-17 DOI: 10.1002/chir.23636

Jony Susanna Kandula, Veera Venkata Satya Prasanna Kumari Rayala, Keyur Parmar, Veerabhadra Swamy Ponnapalli, Mahendar Gantala, Radhakrishnanand P.

{"title":"Enantioselective polar-organic mode high-performance liquid chromatographic separation of lifitegrast on immobilized polysaccharide stationary phase and its application to pH-dependent chiral interconversion studies","authors":"Jony Susanna Kandula, Veera Venkata Satya Prasanna Kumari Rayala, Keyur Parmar, Veerabhadra Swamy Ponnapalli, Mahendar Gantala, Radhakrishnanand P.","doi":"10.1002/chir.23636","DOIUrl":"https://doi.org/10.1002/chir.23636","url":null,"abstract":"(S)-Lifitegrast (LFT) is the novel integrin antagonist, approved by the Food and drug administration, to treat signs and symptoms of dry eye disease. Synthesis of racemic LFT, preparative and analytical enantiomer separation, and chiral interconversion studies are lacking in the literature. Hence, in our study, synthesis of LFT racemate, chiral preparative purification procedure of enantiomer, and comprehensive analytical advancements are focused on rapid enantioselective separation and pH-dependent chiral interconversion studies. The synthesis of LFT racemate employed 2-amino-3-(3-(methylsulfonyl)phenyl)propanoic acid hydrochloride and 2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carbonyl chloride as starting materials. (R)-LFT was isolated from the racemate by preparative chiral HPLC and characterized using Q-TOF, FT-IR, NMR spectroscopy, and chiral HPLC. The purity of (R)-LFT was determined to have an enantiomeric excess of 99.12%. A precise, accurate, rapid HPLC-DAD enantioselective analytical method has been developed on Chiralpak IC [tris(3,5-dichloro phenyl carbamate) immobilized on cellulose] using water and methanol as mobile phase. The chiral interconversion study reveals 0.22% and 0.21% of interconversion of (S)-LFT into (R)-LFT at 80°C in pH 7.4 and 9.5 buffers, respectively, on the 24th day. An alternative route to enantioselective synthesis of LFT enantiomers by chromatographic separation is proposed. The validated enantioselective HPLC method will help to test the regular quality control samples.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 2","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139488492","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

Stereoselectivity of paclobutrazol enantiomers to oxidative stress in wheat 小麦中对映体对氧化应激的立体选择性

IF 2 4区化学

Chirality Pub Date : 2024-01-17 DOI: 10.1002/chir.23638

Chao Yang, Hao Li, Huajun Liang, Bo Huang, Yitao Sun, Wenlong Yang, Yilun Wu, Youhe Cui, Jiangbo Hai, Zhoujia Dong

引用次数: 0

Homochiral zeolites as chiral modifier for voltammetry sensors with high enantioselectivity 将同手性沸石作为手性改性剂用于具有高对映射选择性的伏安法传感器

IF 2.8 4区化学

Chirality Pub Date : 2024-01-15 DOI: 10.1002/chir.23635

Ivan V. Vakulin, Rufina A. Zilberg, Ilnar I. Galimov, Maria A. Sycheva

{"title":"Homochiral zeolites as chiral modifier for voltammetry sensors with high enantioselectivity","authors":"Ivan V. Vakulin, Rufina A. Zilberg, Ilnar I. Galimov, Maria A. Sycheva","doi":"10.1002/chir.23635","DOIUrl":"https://doi.org/10.1002/chir.23635","url":null,"abstract":"Composite enantioselective voltammetry sensors provide a well-known solution for the analysis and discrimination of enantiomerical drugs by voltammetry. The design of such sensor presumes the use of chiral substances to impart chirality to the electrode surface. We present the results of applying a theoretical approach based on simulating the adsorption of analyte enantiomers for preparing high enantioselectivity of pioneering enantioselective sensors using homochiral zeolites as chiral modifiers.We investigated the ability of some homochiral zeolites like CZP, ITV, OSO, STW, MFI, and SOF to act as solid chiral modifiers. Using tryptophan and tyrosine as model objects, we found that the maximum difference between the adsorption energies (ΔEads) of enantiomers on zeolites occurs if enantiomers are placed into the pores of zeolites. The SOF zeolite demonstrates the best enantioselectivity to both amino acids. Moreover, we compared the theoretical results with the experimental enantioselectivity value for tryptophan on a sensor designed as a paste electrode with MFI as the chiral modifier. We found that the calculated value ΔEads(R-S) = −11.0 kJ/mol for MFI, though it is not the best value in the zeolite set considered, it is still enough for the sensor with MFI as the chiral modifier to demonstrate a higher than usual enantioselectivity (ip1/ip2 = 1.58) in an experiment with R- and S- tryptophan as the analyte.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 2","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141985971","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 measure of chiral polyhedrons 手性多面体的手性度量

IF 2 4区化学

Chirality Pub Date : 2024-01-14 DOI: 10.1002/chir.23633

Tsunehisa Kimura, Ryoma Kimura, Yuki Mizukoshi, Kazuya Furusawa

引用次数: 0

Resolution of trans-1,2-cyclohexanedicarboxylic acid containing two carboxylic groups by forming diastereomeric salts based on feeding molar ratio control 基于投料摩尔比控制的非对映体盐法拆分含两个羧基的反式-1,2-环己二羧酸。

IF 2 4区化学

Chirality Pub Date : 2023-12-06 DOI: 10.1002/chir.23634

Xiaoyu Xin, Junjie Zhou, Quan He, Yangfeng Peng, Yongming Wei, Hongliang Zhao, Tianzhong Tong

{"title":"Resolution of trans-1,2-cyclohexanedicarboxylic acid containing two carboxylic groups by forming diastereomeric salts based on feeding molar ratio control","authors":"Xiaoyu Xin, Junjie Zhou, Quan He, Yangfeng Peng, Yongming Wei, Hongliang Zhao, Tianzhong Tong","doi":"10.1002/chir.23634","DOIUrl":"10.1002/chir.23634","url":null,"abstract":"To investigate the thermodynamic and molecular self-assembly mechanism of trans-1,2-cyclohexane dicarboxylic acid containing two carboxylic acid groups in the chiral resolution process, (S)-phenylethylamine was used as the chiral resolving agent. Two stoichiometric salts were formed when the raw materials were fed at different molar ratios: cyclohexane dicarboxylate monophenylethylamine salt and cyclohexane dicarboxylate diphenylethylamine salt. When the molar ratio of the (S)-phenylethylamine to trans-1,2-cyclohexane dicarboxylic acid was less than 3:1, trans-(1S,2S)-cyclohexane dicarboxylic acid was obtained with 97 e.e% purity. But when the molar ratio exceeded 3:1, the product was the racemic trans-(1,2)-cyclohexane dicarboxylic acid. In addition, single crystal structures of more soluble mono-salt, less soluble mono-salt, and less soluble di-salt were obtained. The weak intermolecular interactions and the way of the molecules packing in the crystals were analyzed. The hydrogen bond was stronger in the less soluble salt than that in the more soluble salt. And a “lock-and-key” structure in the hydrophobic layers makes it more tightly packed through the van der Waals interaction, which is responsible for the stability of less soluble salts.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 2","pages":""},"PeriodicalIF":2.0,"publicationDate":"2023-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138497954","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

Separation and simultaneous estimation of enantiomers and Diastereomers of muscarinic receptor antagonist Solifenacin using stability-indicating Normal-phase HPLC technique with chiral stationary phase amylose tris-(3,5-dimethylphenylcarbamate) 手性固定相直链淀粉三-(3,5-二甲基苯基氨基甲酸酯)正相高效液相色谱法分离毒蕈碱受体拮抗剂索利那新对映体和非对映体并同时测定

IF 2 4区化学

Chirality Pub Date : 2023-11-23 DOI: 10.1002/chir.23632

Niroja Vadagam, Sharath Babu Haridasyam, Muvvala Venkatanarayana, Narasimha S. Lakka, Sanjeeva R. Chinnakadoori

{"title":"Separation and simultaneous estimation of enantiomers and Diastereomers of muscarinic receptor antagonist Solifenacin using stability-indicating Normal-phase HPLC technique with chiral stationary phase amylose tris-(3,5-dimethylphenylcarbamate)","authors":"Niroja Vadagam, Sharath Babu Haridasyam, Muvvala Venkatanarayana, Narasimha S. Lakka, Sanjeeva R. Chinnakadoori","doi":"10.1002/chir.23632","DOIUrl":"10.1002/chir.23632","url":null,"abstract":"The R,S-enantiomer impurity and diastereomer impurities (S,S-isomer and R,R-isomer) of the solifenacin (S,R-enantiomer) were effectively separated and quantified simultaneously utilizing normal-phase high-performance liquid chromatography with a chiral stationary phase consisting of amylose tris (3,5-dimethylphenylcarbamate) coated on silica-gel (Chiralpak, AD-H). The enantiomeric and stereo-selective separation was achieved within a run time of 35 minutes using a mobile phase of ‘n-hexane, ethanol, and diethylamine’ in an isocratic elution mode with a detection wavelength of 220 nm. The validation attributes assessed were accuracy (which showed excellent recoveries between 97.5% and 100.4%) and linearity (which was proven in the range of 0.081–1.275 μg.mL−1, with a linear regression of 0.999). The stress testing experiments proved that the developed methodology by the HPLC technique has stability-indicating characteristics, as all closely eluting peak pairs were separated well with a resolution of 2.3 and without any interference. The proposed methodology was highly efficient in separating and simultaneously determining the chiral impurities (enantiomers and diastereomers) of the solifenacin in the release and stability sample analyses of drug substances and tablets in pharmaceutical formulations.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 2","pages":""},"PeriodicalIF":2.0,"publicationDate":"2023-11-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138294813","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

Research on promoting the asymmetric reaction of phenylacetylene with aldehydes by chloramphenicol base ligands 氯霉素基配体促进苯乙炔与醛的不对称反应的研究。

IF 2 4区化学

Chirality Pub Date : 2023-11-16 DOI: 10.1002/chir.23631

Baozhao Lu, Ruifeng Zhang, Congdi Chen, Liming Jin, Jiaqi Xu, Hongjun Yang

引用次数: 0

Theoretical study of the interaction between the antibiotic linezolid and the active site of the 50S ribosomal subunit of the bacterium Haloarcula marismortui 抗生素利奈唑胺与marismortui盐环菌50S核糖体亚基活性位点相互作用的理论研究。

IF 2 4区化学

Chirality Pub Date : 2023-11-14 DOI: 10.1002/chir.23629

Giulia Saneti Grandini, Nelson Henrique Morgon, Aguinaldo Robinson de Souza

{"title":"Theoretical study of the interaction between the antibiotic linezolid and the active site of the 50S ribosomal subunit of the bacterium Haloarcula marismortui","authors":"Giulia Saneti Grandini, Nelson Henrique Morgon, Aguinaldo Robinson de Souza","doi":"10.1002/chir.23629","DOIUrl":"10.1002/chir.23629","url":null,"abstract":"First antibiotic in the oxazolidinone class, linezolid fights gram-positive multiresistant bacteria by inhibiting protein synthesis through its interaction with the 50S subunit of the functional bacterial ribosome. For its antimicrobial action, it is necessary that its chiral carbon located in the oxazolidinone ring is in the S-conformation. Computational calculation at time-dependent density functional theory methodology, ultraviolet–visible (UV–Vis), and electronic circular dichroism spectra was obtained for noncomplexed and complexed forms of linezolid to verify the possible chirality of nitrogen atom in the acetamide group of the molecule. The molecular system has two chiral centers. So, there are now four possible configurations: RR, RS, SR, and SS. For a better understanding of the system, the electronic spectra at the PBE0/6-311++G(3df,2p) level of theory were obtained. The complexed form was obtained from the crystallographic data of the ribosome, containing the S-linezolid molecular system. The computational results obtained for the electronic properties are in good agreement with the experimental crystallographic data and available theoretical results.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 2","pages":""},"PeriodicalIF":2.0,"publicationDate":"2023-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"92152991","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

Enantiomer separation of 2-halomandelic acids via diastereomeric salt formation with chiral N-substituted 2-amino-2-phenylethanols 手性n -取代2-氨基-2-苯基乙醇形成非对映体盐分离2-卤代苯胺酸对映体。

IF 2 4区化学

Chirality Pub Date : 2023-11-13 DOI: 10.1002/chir.23630

Koichi Kodama, Yumi Kondo, Kosei Katayama, Moeka Yanagisawa, Takuji Hirose

引用次数: 0

Lipase mediated new chemo-enzymatic synthesis of (RS)-, (R)-, and (S)-bunolol 脂肪酶介导的新型化学酶合成(RS)-， (R)-和(S)-布诺洛尔。

IF 2 4区化学

Chirality Pub Date : 2023-11-13 DOI: 10.1002/chir.23627

Ravinder Reddy Patlolla, Pulivarthi Deepthi, Gajjala Raveena, Khawlhring Rosangzuala, Somarowthu Tejaswini, Reddy Shetty Prakasham, Linga Banoth

{"title":"Lipase mediated new chemo-enzymatic synthesis of (RS)-, (R)-, and (S)-bunolol","authors":"Ravinder Reddy Patlolla, Pulivarthi Deepthi, Gajjala Raveena, Khawlhring Rosangzuala, Somarowthu Tejaswini, Reddy Shetty Prakasham, Linga Banoth","doi":"10.1002/chir.23627","DOIUrl":"10.1002/chir.23627","url":null,"abstract":"The β-adrenergic receptor blocking agents are an important class of drug molecules. The present study reports a new chemo and chemo-enzymatic synthetic process for (RS)-, (R)-, and (S)-bunolol, one of the potent β-adrenergic receptor blocker. In chemo-enzymatic process, CAL L4777 lipase was employed for enantioselective kinetic resolution to synthesize the enantiopure (R)-alcohol and (S)-ester from the corresponding racemic alcohol. Thereafter, the corresponding (R)-alcohol and deacylated (S)-ester were treated with tert-butylamine to produce (S)- and (R)-bunolol, respectively. In chemical approach, epichlorohydrin (RS-, R-, and S-) was used as a starting material via respective (RS)-, (S)-, and (R)-glycidyl ether as intermediates for synthesis of enantiomeric (RS)-, (R)-, and (S)-bunolol. In comparison between two approaches, it was found that the chemo-enzymatic process was more effective and resulted in enantiomeric excess of 98% with 35% yield.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2023-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"92152990","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