Chirality最新文献_第9页

Preparation of amino acid chiral ionic liquid and visual chiral recognition of glutamine and phenylalanine enantiomers 氨基酸手性离子液体的制备及谷氨酰胺和苯丙氨酸对映体的可视手性识别

IF 2 4区化学

Chirality Pub Date : 2024-04-03 DOI: 10.1002/chir.23665

Luzheng Dong, Jun Wu, Xiashi Zhu

引用次数: 0

Separation of enantiomers of chiral fullerene derivatives through enantioselective encapsulation within an adaptable helical cavity of syndiotactic poly(methyl methacrylate) with helicity memory 通过将手性富勒烯衍生物对映体选择性地封装在具有螺旋记忆功能的辛迪加聚甲基丙烯酸甲酯的可适应螺旋腔内，实现手性富勒烯衍生物对映体的分离。

IF 2 4区化学

Chirality Pub Date : 2024-04-01 DOI: 10.1002/chir.23663

Daisuke Taura, Akiko Minami, Fumihiko Mamiya, Naoki Ousaka, Kenichiro Itami, Eiji Yashima

{"title":"Separation of enantiomers of chiral fullerene derivatives through enantioselective encapsulation within an adaptable helical cavity of syndiotactic poly(methyl methacrylate) with helicity memory","authors":"Daisuke Taura, Akiko Minami, Fumihiko Mamiya, Naoki Ousaka, Kenichiro Itami, Eiji Yashima","doi":"10.1002/chir.23663","DOIUrl":"10.1002/chir.23663","url":null,"abstract":"Optically active left (M)- and right (P)-handed helical syndiotactic poly(methyl methacrylate)s (M- and P-st-PMMAs) with a helicity memory enantioselectively encapsulated the racemic C60 derivatives, such as 3,4-fulleroproline tert-butyl ester (rac-1) and tetraallylated C60 (rac-2), as well as the C60-bound racemic 310-helical peptides (rac-3) within their helical cavities to form peapod-like inclusion complexes and a unique “helix-in-helix” superstructure, respectively. The enantiomeric excess (ee) and separation factor (enantioselectivity) (α) of the analyte 1 (ee = 23%–25% and α = 2.35–2.50) encapsulated within the helical cavities of the M- and P-st-PMMAs were higher than those of the analytes 2 and 3 (ee = 4.3%–6.0% and α = 1.28–1.50). The optically pure (S)- and (R)-1 were found to more efficiently induce an excess one-handed helical conformation in the st-PMMA backbone than the optically pure (S)- and (R)-1-phenylethylamine, resulting in intense mirror-image vibrational circular dichroism (VCD) spectra in the PMMA IR regions. The excess one-handed helices induced in the st-PMMAs complexed with (S)- and (R)-1 were memorized after replacement with the achiral C60, and the complexes exhibited induced electric CDs in the achiral C60 chromophore regions.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 4","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140334880","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

Linear dichroism reveals the perpendicular orientation of DNA bases in the RecA and Rad51 recombinase filaments: A possible mechanism for the strand exchange reaction 线性二色性显示了 RecA 和 Rad51 重组酶丝中 DNA 碱基的垂直取向：链交换反应的可能机制。

IF 2 4区化学

Chirality Pub Date : 2024-04-01 DOI: 10.1002/chir.23664

Masayuki Takahashi, Kentaro Ito, Hiroshi Iwasaki, Bengt Norden

引用次数: 0

Biocatalytic enantioselective synthesis of cenobamate, an antiepileptic drug 生物催化对映体选择性合成抗癫痫药物仙氨酰胺。

IF 2 4区化学

Chirality Pub Date : 2024-03-21 DOI: 10.1002/chir.23660

Vennapusa Haritha, Pulivarthi Deepthi, Rachel Gundamalla, Kommu Nagesh, Suggala V. Satyanarayana, Adari Bhaskar Rao, Sridhar Balasubramanian, Basireddy Venkata Subba Reddy

引用次数: 0

Simultaneous identification and enantioseparation of ofloxacin and duloxetine without the single standard and computational calculation of their inclusion complexes 在没有单一标准的情况下同时鉴定和对映体分离氧氟沙星和度洛西汀，并计算它们的包合物。

IF 2 4区化学

Chirality Pub Date : 2024-03-07 DOI: 10.1002/chir.23661

Lixia Chen, Xiangjun Li

{"title":"Simultaneous identification and enantioseparation of ofloxacin and duloxetine without the single standard and computational calculation of their inclusion complexes","authors":"Lixia Chen, Xiangjun Li","doi":"10.1002/chir.23661","DOIUrl":"10.1002/chir.23661","url":null,"abstract":"Given the markedly different pharmacological activities between enantiomeric isomers, it is crucial to encourage the stereoselective determination of chiral drugs in the biological and pharmaceutical fields, and the combination of drugs makes this analysis more complicated and challenging. Herein, a capillary electrophoresis (CE) method for the enantioseparation of ofloxacin and duloxetine was established, enabling the simultaneous identification of four isomers in nonracemic mixtures with enantiomeric excess (ee%) values exceeding 5%. This was achieved through the integration of theoretical simulation and electron circular dichroism (ECD), all without reliance on individual standards. Molecular modeling explained and verified the migration time differences of these isomers in electrophoretic separation. Moreover, the correlation coefficients (R2) between the enantiomeric peak area differentials and ee% were both above 0.99. Recovery rates were quantified using bovine serum as the matrix, with results ranging from 93.32% to 101.03% (RSD = 0.030) and 92.69% to 100.52% (RSD = 0.028) for these two chiral drugs at an ee value of 23.1%, respectively.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 3","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140058846","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

Enantiomeric separation of thiourea derivatives of naringenin on amylose and cellulose polymeric chromatographic chiral columns 在淀粉和纤维素聚合物色谱手性柱上分离柚皮苷硫脲衍生物的对映体。

IF 2 4区化学

Chirality Pub Date : 2024-03-06 DOI: 10.1002/chir.23659

Imran Ali, Rekia Nabti, Nasser Belboukhari, Khaled Sekkoum, Mohammed El Amin Zaid, Khairedine Kraim, Zeid A. ALOthman, Marcello Locatelli, Ersin Demir

{"title":"Enantiomeric separation of thiourea derivatives of naringenin on amylose and cellulose polymeric chromatographic chiral columns","authors":"Imran Ali, Rekia Nabti, Nasser Belboukhari, Khaled Sekkoum, Mohammed El Amin Zaid, Khairedine Kraim, Zeid A. ALOthman, Marcello Locatelli, Ersin Demir","doi":"10.1002/chir.23659","DOIUrl":"10.1002/chir.23659","url":null,"abstract":"Due to a great demand for amylose and cellulose polymeric chromatographic chiral columns, the enantiomeric separation of thiourea derivatives of naringenin was achieved on the different amylose (Chiralpak-IB) and cellulose chiral (Chiralcel-OJ and Chiralcel-OD-3R) columns with varied chromatographic conditions. The isocratic mobile phases used were ethanol and methanol, where ethanol/hexane and methanol/hexane were used as gradient mode and were prepared in volume/volume relation. The separation and resolution factors for all the enantiomers were in the range of 1.25 to 3.47 and 0.48 to 1.75, respectively. The enantiomeric resolution was obtained within 12 min making fast separation. The docking studies confirmed the chiral recognition mechanisms with binding affinities in the range of −4.7 to −5.7 kcal/mol. The reported compounds have good anticoagulant activities and may be used as anticoagulants in the future. Besides, chiral separation is fast and is useful for enantiomeric separation in any laboratory in the world.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 3","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140038863","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

Enantiomeric purity of synthetic therapeutic peptides: A review 合成治疗肽的对映体纯度：综述。

IF 2 4区化学

Chirality Pub Date : 2024-03-06 DOI: 10.1002/chir.23652

Devendra Badgujar, Sree Teja Paritala, Shubham Matre, Nitish Sharma

{"title":"Enantiomeric purity of synthetic therapeutic peptides: A review","authors":"Devendra Badgujar, Sree Teja Paritala, Shubham Matre, Nitish Sharma","doi":"10.1002/chir.23652","DOIUrl":"10.1002/chir.23652","url":null,"abstract":"Synthetic therapeutic peptides are a complex and popular class of pharmaceuticals. In recent years, peptides with proven therapeutic activity have gained significant interest in the market. The determination of synthetic peptide enantiomeric purity plays a critical role in the evaluation of the quality of the medicine. Since racemization is one of the most common side reactions occurring in AAs or peptides, enantiomeric impurities such as D-isomers can form during the peptide synthesis or can be introduced from the starting materials (e.g., AAs). The therapeutic effect of a synthetic or semi-synthetic bioactive peptide molecule depends on its AA enantiomeric purity and secondary/tertiary structure. Therefore, the enantiomeric purity determination for synthetic peptides is supportive for interpreting unwanted therapeutic effects and determining the quality of synthetic peptide therapeutics. However, enantiomeric purity analysis encounters formidable analytical challenges during chromatographic separation, as D/L isomers have identical physical–chemical properties except stereochemical configuration. To ensure peptides AA stereochemical configuration whether in the free or bound state, sensitive and reproducible quantitative analytical method is mandatory. In this regard, numerous analytical techniques were emerged for the quantification of D-isomeric impurities in synthetic peptides, but still, very few reports are available in the literature. Thus, the purpose of this paper is to provide an overview of the importance, regulatory requirements, and various analytical methods used for peptide enantiomeric purity determination. In addition, we discussed the available literature in terms of enantiomeric impurity detection, common hydrolysis procedural aspects, and different analytical strategies used for sample preparation.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 3","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140048883","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 separations: Recent developments in chiral stationary phases and chromatographic separations of chiral compounds 手性分离：手性固定相和手性化合物色谱分离的最新发展。

IF 2 4区化学

Chirality Pub Date : 2024-02-29 DOI: 10.1002/chir.23657

Oliver Trapp, Nina Berova, Simona Collina, Gennaro Pescitelli

引用次数: 0

Chiroptical properties of membrane glycerophospholipids and their chiral backbones 膜甘油磷脂及其手性骨架的光电特性。

IF 2 4区化学

Chirality Pub Date : 2024-02-28 DOI: 10.1002/chir.23654

Jana Bocková, Adrien D. Garcia, Nykola C. Jones, Søren V. Hoffmann, Cornelia Meinert

{"title":"Chiroptical properties of membrane glycerophospholipids and their chiral backbones","authors":"Jana Bocková, Adrien D. Garcia, Nykola C. Jones, Søren V. Hoffmann, Cornelia Meinert","doi":"10.1002/chir.23654","DOIUrl":"10.1002/chir.23654","url":null,"abstract":"Glycerophospholipid membranes are one of the key cellular components. Still, their species-dependent composition and homochirality remain an elusive subject. In the context of the astrophysical circularly polarized light scenario likely involved in the generation of a chiral bias in meteoritic amino and sugar acids in space, and consequently in the origin of life's homochirality on Earth, this study reports the first measurements of circular dichroism and anisotropy spectra of a selection of glycerophospholipids, their chiral backbones and their analogs. The rather low asymmetry in the interaction of UV/VUV circularly polarized light with sn-glycerol-1/3-phosphate indicates that chiral photons would have been unlikely to directly induce symmetry breaking to membrane lipids. In contrast, the anisotropy spectra of d-3-phosphoglyceric acid and d-glyceraldehyde-3-phosphate unveil up to 20 and 100 times higher maximum anisotropy factor values, respectively. This first experimental report, targeted on investigating the origins of phospholipid symmetry breaking, opens up new avenues of research to explore alternative mechanisms leading to membrane lipid homochirality, while providing important clues for the search for chiral biosignatures of extant and/or extinct life in space, in particular for the ExoMars 2028 mission.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 3","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.23654","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139989430","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

Multidimensional vibrational circular dichroism for insect wings: Comparison of species 昆虫翅膀的多维振动圆二色性：物种比较

IF 2 4区化学

Chirality Pub Date : 2024-02-28 DOI: 10.1002/chir.23655

Hisako Sato, Jun Koshoubu, Sayako Inoué, Izuru Kawamura, Akihiko Yamagishi

{"title":"Multidimensional vibrational circular dichroism for insect wings: Comparison of species","authors":"Hisako Sato, Jun Koshoubu, Sayako Inoué, Izuru Kawamura, Akihiko Yamagishi","doi":"10.1002/chir.23655","DOIUrl":"10.1002/chir.23655","url":null,"abstract":"This study reports the microscopic measurements of vibrational circular dichroism (VCD) on four different insect wings using a quantum cascade laser VCD system equipped with microscopic scanning capabilities (named multi-dimensional VCD [MultiD-VCD]). Wing samples, including (i) beetle, Anomala albopilosa (female), (ii) European hornet, Verspa crabro flavofasciata Cameron, 1903 (female), (iii) tiny dragonfly, Nannophya pygmae Rambur, 1842 (male), and (iv) dragonfly, Symetrum gracile Oguma, 1915 (male), were used in this study. Two-dimensional patterns of VCD signals (~10 mm × 10 mm) were obtained at a spatial resolution of 100 μm. Measurements covered the absorption peaks assigned to amides I and II in the range of 1500–1740 cm−1. The measurements were based on the enhancement of VCD signals for the stereoregular linkage of peptide groups. The patterns were remarkably dependent on the species. In samples (i) and (ii), the wings comprised segregated domains of protein aggregates of different secondary structures. The size of each microdomain was approximately 100 μm. In contrast, no clear VCD spectra were detected in samples (iii) and (iv). One possible reason was that the chain of stereoregular polypeptides was too short to achieve VCD enhancement in samples (iii) and (iv). Notably, the unique features were only observed in the VCD spectra because the IR spectra were nearly the same among the species. The VCD results hinted at the connection of protein microscopic structures with the wing flapping mechanisms of each species.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 3","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139989431","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