IF 2.8 4区化学

Chirality Pub Date : 2024-11-12 DOI: 10.1002/chir.70006

Francesca Romana Mammone, Daniele Sadutto, Roberto Cirilli

{"title":"Multiwavelength Optical Rotation Detection: An Effective Approach for the Recognition of Analytical and Semi-Preparative HPLC Enantioseparation of the Chiral Pheromone Olean and Its Stereochemical Characterization","authors":"Francesca Romana Mammone, Daniele Sadutto, Roberto Cirilli","doi":"10.1002/chir.70006","DOIUrl":"10.1002/chir.70006","url":null,"abstract":"<div>\u0000 \u0000 Olean is the chiral spiroacetal sex pheromone of the female olive fruit fly Bactrocera oleae. Laboratory tests have demonstrated that the (R)-(−)-olean enantiomer is active on males, whereas females respond to (S)-(+)-olean. Here we present the first HPLC enantioseparation of olean using polysaccharide derivatives as chiral stationary phases and a polarimetric detector equipped with a micro-flow cell capable of detecting optical rotation at six different wavelengths. Unlike blind UV detection, the polarimetric detector allows the chiral spiroacetal, which lacks a chromophore, to be detected as bisegnate peaks, indicating the opposite sign of the optical rotation. The HPLC enantioseparation was optimized on the coated type amylose-based Chiralpak AS-H CSP using a mobile phase consisting of n-hexane-2-propanol 99.99:0.01 (v/v). These conditions were scaled up to a semi-preparative level and allowed resolution of 2.5 mg of racemic sample in 5 min. Multiwavelength optical rotation detection during HPLC enantioseparation of racemic samples provides a direct readout of the stereochemistry of olean and allows tracking of virtual optical rotation dispersion curves without the need for preliminary collection of enantiomeric samples by semi-preparative HPLC.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142614426","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

Emergence of Optical Activity and Surface Morphology Changes in Racemic Amino Acid Films Under Circularly Polarized Lyman-α Light Irradiation 外消旋氨基酸薄膜在圆偏振莱曼-α光照射下出现的光学活性和表面形态变化

IF 2.8 4区化学

Chirality Pub Date : 2024-11-11 DOI: 10.1002/chir.70004

Masahiro Kobayashi, Jun-ichi Takahashi, Hiroshi Ota, Koichi Matsuo, Mohamed I. A. Ibrahim, Taketoshi Minato, Gen Fujimori, Masahiro Katoh, Kensei Kobayashi, Yoko Kebukawa, Hiroaki Nakamura

{"title":"Emergence of Optical Activity and Surface Morphology Changes in Racemic Amino Acid Films Under Circularly Polarized Lyman-α Light Irradiation","authors":"Masahiro Kobayashi, Jun-ichi Takahashi, Hiroshi Ota, Koichi Matsuo, Mohamed I. A. Ibrahim, Taketoshi Minato, Gen Fujimori, Masahiro Katoh, Kensei Kobayashi, Yoko Kebukawa, Hiroaki Nakamura","doi":"10.1002/chir.70004","DOIUrl":"10.1002/chir.70004","url":null,"abstract":"The homochirality of life remains one of the most enigmatic issues in the study of the origin of life. A proposed mechanism for symmetry breaking involves irradiation by circularly polarized light (CPL). To investigate the photoreaction of amino acids under CPL irradiation, a vacuum ultraviolet (VUV) CPL irradiation system was developed at the synchrotron light source UVSOR-III. Hydrogen Lyman-α CPL (121.6 nm) is considered a potential asymmetric source in space. Therefore, racemic alanine film samples were irradiated with Lyman-α CPL to explore the photoreaction of biomolecules. Circular dichroism (CD) spectra measurements revealed that irradiation with right- (left-) handed CPL induced a positive (negative) anisotropy factor g in the wavelength range of 180–240 nm. However, the spectra differed from those of enantiopure alanine, exhibiting broad wavelength ranges and no sign change. Liquid chromatography-mass spectrometry (LC–MS) measurements indicate formation of larger molecules, such as oligomeric alanine adducts or modified oligomers after the Lyman-α CPL irradiation. Additionally, CPL irradiation considerably changes the microstructure of the alanine film surface, leading to the formation of circular network aggregates on the scale of 100 nm. The morphology changes in the alanine film and/or the formation of the larger molecules could be possible causes of the modified anisotropy factor spectra compared to those of enantiopure alanine. These findings highlight the need for further research on the photoreaction of biomolecules in solid states under VUV CPL irradiation, particularly in the photoionization energy range, to validate the cosmic scenario of homochirality.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.70004","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142614420","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

Proceedings From 33rd Symposium on Chirality 2023, Rome, Italy 第 33 届手性研讨会论文集 2023 年，意大利罗马。

IF 2.8 4区化学

Chirality Pub Date : 2024-11-08 DOI: 10.1002/chir.70005

Alessa Ciogli, Lorenzo Di Bari, Francesco Zinna, Nina Berova, Gennaro Pescitelli, Oliver Trapp, Simona Collina

引用次数: 0

Resolution and Absolute Configuration of Fargesin Enantiomers Fargesin 对映异构体的解析和绝对构型。

IF 2.8 4区化学

Chirality Pub Date : 2024-11-06 DOI: 10.1002/chir.70003

Eloá R. Mestriner, Eric Y. Lee, Camila L. Cunha, Victor M. S. Sousa, Isabele R. Nascimento, João M. Batista Jr

引用次数: 0

Chiroptical Sensing of Amines With Isatins 用异肽对胺进行光电传感

IF 2.8 4区化学

Chirality Pub Date : 2024-10-24 DOI: 10.1002/chir.70002

F. Safia Kariapper, Flavia Miccolis, Samantha L. Pilicer, Christian Wolf

引用次数: 0

An Enzymatic Method to Obtain Enantiopure 3-Pyridyl and Substituted Phenyl Alanine 获得不纯 3-吡啶基和取代苯基丙氨酸的酶法。

IF 2.8 4区化学

Chirality Pub Date : 2024-10-22 DOI: 10.1002/chir.70000

Fan Jiang, Ke-Xin Chen, Jiang-Mei Xiang, Yong-Cun Shen

引用次数: 0

Structure Assessment and Impacts of Lipids' Chemistry on the Structuration of Polyhydroxyalkanoate Biosynthesized by Bacillus licheniformis AZU-A5 地衣芽孢杆菌 AZU-A5 生物合成的聚羟基烷酸酯的结构评估及脂类化学成分对其结构的影响

IF 2.8 4区化学

Chirality Pub Date : 2024-10-15 DOI: 10.1002/chir.23722

Mohamed I. A. Ibrahim, Mahmoud E. Esmael, Tamer R. Elmashi, Tatsuki Haga, Reda A. Bayoumi, Mohamed M. Eldanasoury, Mahmoud R. Sofy, Koichi Matsuo, Abdelrahman M. Khattab

{"title":"Structure Assessment and Impacts of Lipids' Chemistry on the Structuration of Polyhydroxyalkanoate Biosynthesized by Bacillus licheniformis AZU-A5","authors":"Mohamed I. A. Ibrahim, Mahmoud E. Esmael, Tamer R. Elmashi, Tatsuki Haga, Reda A. Bayoumi, Mohamed M. Eldanasoury, Mahmoud R. Sofy, Koichi Matsuo, Abdelrahman M. Khattab","doi":"10.1002/chir.23722","DOIUrl":"https://doi.org/10.1002/chir.23722","url":null,"abstract":"The current study exploited cheese whey supernatant (CWS) as a renewable resource for polyhydroxyalkanoates (PHAs) formation. Structure identification and investigating the influence of lipid membranes' chemistry on PHA structuration were detailed. Approximately 66 bacterial isolates from dairy products companies in Egypt were screened for PHA production, and the bacterial isolate AZU-A5, identified as Bacillus licheniformis strain AZU-A5, showed the highest production PHA 0.93 g L−1) using whey lactose. The highest PHA rate in the individual design was 1.59 g L−1 with a recovery yield of 33.08% (w w−1), while the production rate in the statistical design reached 1.75 g L−1 PHA and 51.60% PHA content. Structurally, the PHA was identified as polyhydroxy-3R-butyrate (R-PH3B). The fibrous texture by SEM highlighted the self-assembly of PHB. The CD analysis of the PHA films suggested favorable hydrophobic interactions between lipids and PHB. Higher lipid contents not only caused a decrement in the CD signal of PHB but also bathochromic effects occurred. The chain length of lipids exerted high impacts on interactions (CD) and structuration of PHB (Δλ). The unsaturation showed little influence on CD and negligible effect on Δλ, while the head group exerted no effect on CD with a considerable impact on Δλ.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 10","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.23722","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142443375","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

Optical Activities of Organic Crystals: Crystal Orbital Formulation of Anisotropic Gyration 有机晶体的光学活性：各向异性回旋的晶体轨道模型

IF 2.8 4区化学

Chirality Pub Date : 2024-10-15 DOI: 10.1002/chir.23719

Masashi Hatanaka

引用次数: 0

Enantioselective Separation and Pharmacokinetics of a Chiral 1,4-Dihydropyrimidine Derivative in Rats: A Combined Chromatography and Docking Approach 手性 1,4-二氢嘧啶衍生物在大鼠体内的对映选择性分离和药代动力学：色谱与对接相结合的方法

IF 2.8 4区化学

Chirality Pub Date : 2024-10-13 DOI: 10.1002/chir.23723

Chiriki Devi Sri, Syed Faizan, Muttavarapu Rohit Chandra, B. R. Prashantha Kumar, B. M. Gurupadayya

{"title":"Enantioselective Separation and Pharmacokinetics of a Chiral 1,4-Dihydropyrimidine Derivative in Rats: A Combined Chromatography and Docking Approach","authors":"Chiriki Devi Sri, Syed Faizan, Muttavarapu Rohit Chandra, B. R. Prashantha Kumar, B. M. Gurupadayya","doi":"10.1002/chir.23723","DOIUrl":"https://doi.org/10.1002/chir.23723","url":null,"abstract":"<div>\u0000 \u0000 Chirality in 1,4-Dihydropyrimidines influences their pharmacological properties and synthetic strategies. Enantiomers of chiral drugs often exhibit different pharmacokinetic profiles. Therefore, separating and studying individual enantiomers is crucial to optimize drug efficacy and safety. Enantiomeric separation of ±4-(4-chlorophenyl)-6-methyl-2-oxo-N-(O-toyl)-1,2,3,4-tetrahydropyrimidine-5-carboxamide (DP-1), which is a 1,4-Dihydropyrimidine derivative is achieved on CHIRALCEL® OD-H column (particle size: 5 μm, inner diameter: 4.6 mm, length:150 mm), following by investigating the kinetic properties of (R) and (S) enantiomers. The separation was achieved with a mobile phase composed of 70% (v/v) isopropyl alcohol and 30% (v/v) n-hexane. For the bioanalytical study, acetonitrile was used to precipitate the rat plasma samples and validated the method according to USFDA guidelines. The validated bioanalytical method was then successfully applied to determine the pharmacokinetic parameters of the drug in biological samples. Molecular modeling techniques, specifically docking simulations, were employed to predict the elution order of DP-1 enantiomers. The docking results revealed moderate binding interactions between the enantiomers and the chiral stationary phase (CSP), which aligns with the theoretical expectation that stronger interactions lead to longer retention times on the column.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 10","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142435688","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 Self-Sorting Process With C2 Symmetric Bisimidazoline Ligands 使用 C2 对称双咪唑啉配体的手性自分选过程

IF 2.8 4区化学

Chirality Pub Date : 2024-10-10 DOI: 10.1002/chir.23720

Caitlyn Dussart, Aline Maisse-François, Stéphane Bellemin-Laponnaz

引用次数: 0

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