Chirality最新文献_第7页

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

Total synthesis of (6R,12R)-6,12-dimethylpentadecan-2-one, the sex pheromone of Diabrotica balteata LeConte Diabrotica balteata LeConte 的性信息素 (6R,12R)-6,12-dimethylpentadecan-2-one 的全合成。

IF 2 4区化学

Chirality Pub Date : 2024-02-27 DOI: 10.1002/chir.23658

Jianwei Wu, Chuanwen Lin, Dan Liu, Qinghua Bian, Min Wang, Jiangchun Zhong

引用次数: 0

Chiral recognition and discrimination studies of tyrosine enantiomers on (−)-18-crown-6-tetracarboxylic acid as a chiral selector by nuclear magnetic resonance spectroscopy and docking simulations 通过核磁共振波谱和对接模拟，研究(-)-18-冠醚-6-四羧酸作为手性选择剂的酪氨酸对映体的手性识别和区分。

IF 2 4区化学

Chirality Pub Date : 2024-02-26 DOI: 10.1002/chir.23656

Gaeun Lee, Suraj Adhikari, Sunho Lee, Jeong Yeon Lee, Yun-Cheol Na, Wonjae Lee, Eunjung Bang

{"title":"Chiral recognition and discrimination studies of tyrosine enantiomers on (−)-18-crown-6-tetracarboxylic acid as a chiral selector by nuclear magnetic resonance spectroscopy and docking simulations","authors":"Gaeun Lee, Suraj Adhikari, Sunho Lee, Jeong Yeon Lee, Yun-Cheol Na, Wonjae Lee, Eunjung Bang","doi":"10.1002/chir.23656","DOIUrl":"10.1002/chir.23656","url":null,"abstract":"Considering the substantial significance of chiral biomolecules, such as amino acids, in our daily routines, we performed chiral recognition and discrimination of tyrosine (Tyr) enantiomers on (−)-(18-crown-6)-2,3,11,12-tetracarboxylic acid [(−)-18-C-6-TA] as crown-ether type chiral selector (CS) by nuclear magnetic resonance (NMR) spectroscopy and docking simulations. In this study, successful discrimination of the enantiomers of Tyr was achieved, as evidenced by the proton chemical shift differences (ΔΔδ) of Tyr enantiomers observed in the 1H NMR spectra with (−)-18-C-6-TA CS. We compared the results of these two techniques with the findings obtained from high performance liquid chromatography (HPLC) investigations. In both NMR and HPLC experimental and docking simulation studies, a stronger interaction between the L-Tyr enantiomer with (−)-18-C-6-TA CS than the D-Tyr was consistently observed. Also, the binding energy differences (ΔΔEL-D) found in simulation data that correspond to enantioselectivity aligned well with the NMR experimental result.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 3","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139971077","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

Mid-IR and CH stretching vibrational circular dichroism spectroscopy to distinguish various sources of chirality: The case of quinophaneoxazoline based ruthenium(II) complexes 用中红外光谱和 CH 伸展振动圆二色光谱区分手性的各种来源：以喹吩恶唑啉基钌（II）配合物为例。

IF 2 4区化学

Chirality Pub Date : 2024-02-26 DOI: 10.1002/chir.23649

Marco Fusè, Giuseppe Mazzeo, Sergio Abbate, Renzo Ruzziconi, Julien Bloino, Giovanna Longhi

引用次数: 0

Study on the anti-cancer activity of α-phenethylamine ferrocenecarboxylic acid co-crystals α-苯乙胺二茂铁羧酸共晶体的抗癌活性研究

IF 2 4区化学

Chirality Pub Date : 2024-02-25 DOI: 10.1002/chir.23653

Liao Youyin, Ma Yuexing, Chen Jiahao, Qian Kun, Yang Jie, Pan Rongbin, Xu Yiyong

{"title":"Study on the anti-cancer activity of α-phenethylamine ferrocenecarboxylic acid co-crystals","authors":"Liao Youyin, Ma Yuexing, Chen Jiahao, Qian Kun, Yang Jie, Pan Rongbin, Xu Yiyong","doi":"10.1002/chir.23653","DOIUrl":"10.1002/chir.23653","url":null,"abstract":"Ferrocene derivatives show a wide range of pharmacological activities in the medical field, especially in the anti-tumor field, and can be used as candidate drugs or lead compounds for the treatment of tumors and other diseases. And α-phenethylamine is an important intermediate for the preparation of fine chemical products. (R)-(+)-1-Phenethylamine ferrocenecarboxylic acid/(S)-(−)-1-phenethylamine ferrocenecarboxylic acid were prepared, named compounds 1 and 2, respectively. Single crystal X-ray diffraction showed that compounds 1 and 2 crystallized in the orthorhombic system space group P212121, and the crystal structures of compounds 1 and 2 exhibited mirror symmetry. The inhibitory effect of two compounds on SW480, MDA-MB-231, and H1299 cells was tested by MTT colorimetry. The IC50 values of the compounds against cancer cells were also calculated. The anti-cancer effect was more pronounced for compounds in the S-configuration. Compound 2 made the wild-type cancer cells undergo apoptosis, thus preventing cancer; it also had the function of helping the cell gene repair defects.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 3","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139968779","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

Correction to “Effect of chirality in the supramolecular polymerization of N-annulated perylenediimides: Cancelling pathway complexity” 对 "手性在 N-annulated perylenediimides 超分子聚合中的影响：消除途径的复杂性"

IF 2 4区化学

Chirality Pub Date : 2024-02-21 DOI: 10.1002/chir.23650

引用次数: 0

Correction to “Switching the on-surface orientation of oxygen-functionalized helicene” 对 "改变氧官能化螺旋烯的表面取向 "的更正

IF 2 4区化学

Chirality Pub Date : 2024-02-21 DOI: 10.1002/chir.23651

引用次数: 0