Mid-IR and CH stretching vibrational circular dichroism spectroscopy to distinguish various sources of chirality: The case of quinophaneoxazoline based ruthenium(II) complexes
Chirality. 2024 Mar;36(3):e23649. doi: 10.1002/chir.23649.ABSTRACTFive diastereomers of ruthenium(II) complexes based on quinolinophaneoxazoline ligands were investigated by vibrational circular dichroism (VCD) in the mid-IR and CH stretching regions. Diastereomers differ in three sources of chirality: the planar chirality of the quinolinophane moiety, the central chirality of an asymmetric carbon atom of the oxazoline ring, and the chirality of the ruthenium atom. VCD, allied to DFT calculations, has been found to be effective in disentangling the various forms of chirality. In particular, a VCD band is identified in the ...
Source: Chirality - February 27, 2024 Category: Molecular Biology Authors: Marco Fus è Giuseppe Mazzeo Sergio Abbate Renzo Ruzziconi Julien Bloino Giovanna Longhi Source Type: research
Study on the anti-cancer activity of α-phenethylamine ferrocenecarboxylic acid co-crystals
Chirality. 2024 Mar;36(3):e23653. doi: 10.1002/chir.23653.ABSTRACTFerrocene 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 ...
Source: Chirality - February 26, 2024 Category: Molecular Biology Authors: Liao Youyin Ma Yuexing Chen Jiahao Qian Kun Yang Jie Pan Rongbin Xu Yiyong Source Type: research
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
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 1 H 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 correspon...
Source: Chirality - February 26, 2024 Category: Molecular Biology Authors: Gaeun Lee Suraj Adhikari Sunho Lee Jeong Yeon Lee Yun-Cheol Na Wonjae Lee Eunjung Bang Source Type: research
Study on the anti-cancer activity of α-phenethylamine ferrocenecarboxylic acid co-crystals
Chirality. 2024 Mar;36(3):e23653. doi: 10.1002/chir.23653.ABSTRACTFerrocene 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 ...
Source: Chirality - February 26, 2024 Category: Molecular Biology Authors: Liao Youyin Ma Yuexing Chen Jiahao Qian Kun Yang Jie Pan Rongbin Xu Yiyong Source Type: research
Effect of chirality in the supramolecular polymerization of N-annulated perylenediimides: Cancelling pathway complexity
Chirality. 2024 Feb;36(2):e23639. doi: 10.1002/chir.23639.ABSTRACTHerein, the synthesis of two chiral NPBIs, (S)-1 and (R)-1, is reported and their self-assembling features investigated. The reported NPBIs form chiral supramolecular polymers with a rich dichroic pattern by the π-stacking of the aromatic backbones and the formation of an array of H-bonds between the amide functional groups. Furthermore, the peripheral 3,4,5-trialkoxy benzamide groups can form seven-membered pseudocycles by the intramolecular H-bonding interaction between the NH of the peripheral amides and one of the carbonyls of the imide units thus yield...
Source: Chirality - February 22, 2024 Category: Molecular Biology Authors: Elisa E Greciano Alfonso J Schwalb Luis S ánchez Source Type: research
Construction of high-throughput magnetic circular dichroism measurement system and its application to research on magnetic and optical properties of phthalocyanine complexes
Chirality. 2024 Feb;36(2):e23648. doi: 10.1002/chir.23648.ABSTRACTMagnetic circular dichroism (MCD) spectroscopy is a powerful method for evaluating the electronic structure and magnetic and optical properties of molecules. In particular, MCD measurements have been performed on phthalocyanines and porphyrins with various central metal ions, axial ligands, and substituents to elucidate their properties. It is essential to develop a robust high-throughput technique to perform these measurements comprehensively and efficiently. However, MCD spectroscopy requires very high optical quality for each component of the instrument, ...
Source: Chirality - February 22, 2024 Category: Molecular Biology Authors: Satoko Suzuki Akio Kaneta Anas Santria Kengo Yoshida Taiji Oyama Yoshitane Imai Ken-Ichi Akao Naoto Ishikawa Source Type: research
Advancement in chiral heterocycles for the antidiabetic activity
This study focuses on the current trends in the use of chiral heterocycles in drug design and the creation of several powerful and competent candidates for diabetic illnesses.PMID:38384150 | DOI:10.1002/chir.23637 (Source: Chirality)
Source: Chirality - February 22, 2024 Category: Molecular Biology Authors: Tinku Gupta Dimpy Rani Lalit Mohan Nainwal Reena Badhwar Source Type: research
Stereoselectivity of paclobutrazol enantiomers to oxidative stress in wheat
This study provided a theoretical basis for the selective activity of chiral pesticides and the development of chiral pesticide monomers.PMID:38384151 | DOI:10.1002/chir.23638 (Source: Chirality)
Source: Chirality - February 22, 2024 Category: Molecular Biology Authors: Chao Yang Hao Li Huajun Liang Bo Huang Yitao Sun Wenlong Yang Yilun Wu Youhe Cui Jiangbo Hai Zhoujia Dong Source Type: research
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
Chirality. 2024 Feb;36(2):e23636. doi: 10.1002/chir.23636.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 racema...
Source: Chirality - February 22, 2024 Category: Molecular Biology Authors: Jony Susanna Kandula Veera Venkata Satya Prasanna Kumari Rayala Keyur Parmar Veerabhadra Swamy Ponnapalli Mahendar Gantala Radhakrishnanand P Source Type: research
Chiral measure of chiral polyhedrons
Chirality. 2024 Feb;36(2):e23633. doi: 10.1002/chir.23633.ABSTRACTTo quantify chiral shape, a tensor describing the particle shape has been proposed. This tensor, named the shape tensor (S-tensor), is an analog of the hydrodynamic tensor that relates the rotational and translational motions of particles in a liquid. The determinant of the S-tensor, named chirality measure density (CMD), was calculated for chiral tetrahedrons and octahedrons. It was found that CMD is opposite in sign when the mirror images are chiral to each other and vanishes when they are achiral. Therefore, the CMD is a good measure to distinguish the mi...
Source: Chirality - February 22, 2024 Category: Molecular Biology Authors: Tsunehisa Kimura Ryoma Kimura Yuki Mizukoshi Kazuya Furusawa Source Type: research
Chiral acidic molecularly imprinted polymer for enantio-separation of norepinephrine racemate
Chirality. 2024 Feb;36(2):e23645. doi: 10.1002/chir.23645.ABSTRACTWe are looking into how well a copolymeric material made of poly (maleic acid-co-4-vinylpyridine) cross-linked with divinylbenzene can separate L-norepinephrine (L-NEP) from (±)-NEP. The initial step in this direction was the synthesis and subsequent analysis of L-NEP-maleimide chiral derivative. A 4-vinylpyridine/divinylbenzene combination was copolymerized with the resultant chiral maleimide. After heating the polymer materials in a high-alkaline environment to breakdown the connecting imide bonds, they were acidified in an HCl solution to eliminate the i...
Source: Chirality - February 22, 2024 Category: Molecular Biology Authors: May Abdullah Abomuti Source Type: research
Switching the on-surface orientation of oxygen-functionalized helicene
Chirality. 2024 Feb;36(2):e23642. doi: 10.1002/chir.23642.ABSTRACTHelicenes represent an important class of chiral organic material with promising optoelectronic properties. Hence, functionalization of surfaces with helicenes is a key step toward new organic materials devices. The deposition of a heterohelicene containing two furano groups and two hydroxyl groups onto copper(111) surface in ultrahigh vacuum leads to different adsorbate modifications. At low coverage and low temperature, the molecules tend to lie on the surface in order to maximize van der Waals contact with the substrate. Thermal treatment leads to deproto...
Source: Chirality - February 22, 2024 Category: Molecular Biology Authors: Jan Voigt Mohammed Hasan Christian W äckerlin Anil V Karnik Karl-Heinz Ernst Source Type: research
Resolution of N-acetyl-DL-methionine methyl ester by the lipase from Brucella thiophenivorans
In this study, lipase-catalyzed resolution of N-acetyl-DL-methionine methyl ester (N-Ac-DL-MetOMe) was evaluated. A lipase from Brucella thiophenivorans was prone to exhibit high activity and excellent enantioselectivity toward N-Ac-DL-MetOMe to produce the key chiral intermediate N-acetyl-L-methionine methyl ester (N-Ac-L-MetOMe). The results showed that the enzymatic reaction was carried out in 100 g/L racemic substrate for 2 h, the conversion reached 51.3%, the enantiomeric excess value N-Ac-L-MetOMe exceeded 99%, and the enantiomeric ratio value >200. Therefore, the lipase from B. thiophenivorans has potential prosp...
Source: Chirality - February 22, 2024 Category: Molecular Biology Authors: Xiaojun Li Qi Li Liying Yang Liqin Huang Chenchen Peng Jianyong Zheng Source Type: research
Chiral separation of propranolol by electrokinetic chromatography using nanodiamonds and human serum albumin as a pseudo-stationary phase in river water
In this study, R- and S-propranolol were determined in river samples by electrokinetic chromatography (EKC) using nanodiamonds (NDs) and human serum albumin (HSA) as a pseudo-stationary phase in order to achieve enantioseparation. Previously, river samples were preconcentrated using a column filled with Amberlite® IR-120 and Dowex® 50WX8 resins. The setting up of influential factors such as temperature, voltage, pH, and HSA and NDs concentration is accurately described along this manuscript. A multivariate study and optimization was carried out to obtain the enantioseparation of propranolol (Rs = 2.91), which was reached...
Source: Chirality - February 22, 2024 Category: Molecular Biology Authors: Ver ónica M Lanaro Lorena L Sombra Jorgelina C Altamirano C ésar A Almeida Patricia W Stege Source Type: research
Size dependence of optical activities in helical polymers
This study investigates the discrepancy in optical rotatory strength between local and global structures using a right-handed helical polyacetylene model. The chirality is examined through density functional theory (DFT) calculations. The analysis reveals that, at higher degrees of polymerization, the contribution of chirality from the helical strand generally surpasses the partial chirality from the local structure. The ratio of local contribution to total contribution is deduced within the framework of crystal orbital theory, and a numerical method using Wannier functions is presented for evaluation.PMID:38384158 | DOI:1...
Source: Chirality - February 22, 2024 Category: Molecular Biology Authors: Masashi Hatanaka Source Type: research
