Article
Chemistry, Multidisciplinary
Jiayao Li, Changwei Wang, Yirong Mo
Summary: In this study, the nature and selectivity of hydrogen bonds inside cryptands were analyzed to understand the binding between cryptands and anions. It was found that the strength of hydrogen bonds is determined by electrostatic attraction, while the anion preferences are governed by Pauli exchange repulsion and electrostatic interaction. Different conformers of cryptands and the size of anions affect the selectivity through the relaxation of Pauli repulsion and reduction of electrostatic attraction. The rigidity of cages and the binding sites of anions also play a role in determining the selectivity.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Jie Shen, Ruijuan Ye, Zhiwei Liu, Huaqiang Zeng
Summary: This study introduces a novel biomimetic channel system that can replicate the high selectivity and permeation rate of natural protein channels. These artificial channels demonstrate high selectivity and fast proton transport rate, and utilize a unique proton transport mechanism to facilitate transmembrane flux.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Jonathan Alvarez-Garcia, Victor Rubio-Pisabarro, Luis Garcia-Rio, Maria Magdalena Cid
Summary: Proton transfer equilibria play a key role in various biological and pharmaceutical processes. The behavior of chiral pyrido-cyclophanes in the presence of different acids was studied, revealing double protonation and formation of cascade ion-pairs. Water presence promoted the crystallization of intermediates not corresponding to those in solution, and proton transfer from acid to pyridine was found to occur regardless of acid's pKa. The hydrogen position after proton transfer equilibria was elucidated by diagnostic signals in ECD of cascade complexes.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Sebastian Dengler, Ryan T. Howard, Vasily Morozov, Christos Tsiamantas, Wei-En Huang, Zhiwei Liu, Christopher Dobrzanski, Vojislava Pophristic, Sophie Brameyer, Celine Douat, Hiroaki Suga, Ivan Huc
Summary: Expanding the chemical diversity of peptide macrocycle libraries through the inclusion of a large aromatic helical foldamer has been implemented. A hybrid macrocyclic nanomolar binder to the C-lobe of the E6AP HECT domain was selected, and its crystal structure and molecular dynamics simulations revealed an intriguing reciprocal helical folding of the peptide and foldamer. The results represent a significant extension in the chemical space amenable to display selection and highlight the potential benefits of incorporating an aromatic foldamer into a peptide macrocycle for protein recognition.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Ya-Zhou Liu, Xiao Mu, Cheih-Kai Chan, Koen Robeyns, Cheng-Chung Wang, Michael L. Singleton
Summary: The researchers synthesized a heptameric sheet-like aromatic oligoamide foldamer with ferrocene as a turn unit and found strong interactions with water. These interactions limit the fluxional processes resulting from the flexible ferrocene unit.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Giuseppe Ermondi, Francesca Lavore, Maura Vallaro, Guido Tiana, Francesca Vasile, Giulia Caron
Summary: The study characterized the conformational ensembles of the bRo5 drug rifampicin in different environments and found that its conformational behavior in solution and in the solid state is not superposable. Dynamic intramolecular hydrogen bonds were identified through NMR spectroscopy but were not found in X-ray structures, and it was revealed that they do not provide rifampicin with chameleonic properties. Overall, the unique properties of rifampicin, such as cell permeability and lack of chameleonic behavior, can be assessed by analyzing experimental 3D structures.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Physical
Yunhe Li, Yi Zhou, Jie Zhang, Ruiyu Liu, Xiang Zhao, Youliang Wang
Summary: This study presents a comprehensive density functional theory (DFT) study on gold-catalyzed domino cyclization to spiroindolines. The diastereoselectivity of this reaction is explained by both electronic and geometric factors, providing guidance for the development of more effective stereochemistry controlled by a counterion effect in transition metal complexes.
CATALYSIS SCIENCE & TECHNOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Lu Zheng, Shengzhu Guo, Chu Wang, Yanru Wang, Yanqing Fan, Xuebo Chen, Kun Zhang, Hua Jiang
Summary: The intensity of intramolecular helix chiral communication between the two QOFs is dependent on the length of the linkers, with shorter linkers leading to increased interaction between the two QOFs.
Article
Chemistry, Multidisciplinary
Oscar Francesconi, Francesco Milanesi, Cristina Nativi, Stefano Roelens
Summary: The study introduces a biomimetic receptor with unprecedented affinity for recognizing GlcNAc(2) in water, showing great selectivity among structurally related disaccharides and complete discrimination between mono- and disaccharides. Molecular modeling calculations supported by NOE data provided insights into the binding mode and origin of the affinities and selectivities exhibited by the receptor.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Engineering, Chemical
Biplab K. Mahata, Sue-Min Chang, Purnendu Bose
Summary: The Cu-WBA resin achieves efficient phosphate adsorption and regeneration by introducing Cu2+ ions, exhibiting high selectivity and tolerance. During adsorption, Cu2+ ions drive phosphate diffusion and induce phosphate bonding with multiple groups, showing high entropy and exergonicity. In regeneration, Cu2+ can transform to Cu-O, facilitating phosphate desorption.
SEPARATION AND PURIFICATION TECHNOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Taichi Koike, Takeaki Iwamoto
Summary: In this study, overcrowded 1-amino-2-boryldisilenes were synthesized through a direct reaction, exhibiting strong polarization and characteristic long-wavelength absorption.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Alex Iglesias-Reguant, Judyta Zielak-Milewska, Tomasz Misiaszek, Robert Zalesny, Josep M. Luis, Borys Osmialowski
Summary: This study investigates the halogen-bonding interactions between a pyridine-functionalized fluoroborate dye and perfluorohaloarenes using fluorescence spectroscopy. The results indicate that only the complex formed between C6F5I and the emissive dye is stable, and halogen-bonding interactions lead to significant Stokes shifts for the pi pi * band. Experimental evidence also shows that the emission of this complex is suppressed due to a simultaneous decrease in radiative decay rate constant and an increase in nonradiative decay rate constant.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yoshihiro Hamada, Yuichiro Tokoro, Toshiyuki Oyama
Summary: Diformylated N-Hetero-ortho-phenylene hexamers were synthesized from 2,3-dichloropyrydine through palladium-catalyzed coupling reactions and deprotection. Chiral self-sorting occurred by macrocyclization with para-phenylenediamine in the presence of para-toluenesulfonic acid, revealing a homochiral structure containing N-oP(6) moieties. Using specific chiral acids could induce a chiral bias in the helical folding of N-oP(6) moieties and achieve planar chiral self-sorting of the bridged moieties.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Rafal Wysokinski, Mariusz Michalczyk, Wiktor Zierkiewicz, Steve Scheiner
Summary: The study assesses the ability of TrCl4- (Tr = Al, Ga, In, Tl) to form triel bonds with NH3 and CN- anions through quantum calculations in both gas phase and aqueous medium. Despite the energy investment, strong exothermic complexation reactions are observed, particularly in water.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2021)
Article
Chemistry, Multidisciplinary
Kyle R. Strom, Jack W. Szostak
Summary: In this study, six oligoarylacetylene trimers composed of aniline and benzaldehyde subunits were examined, and it was found that reversible covalent bonds could guide the formation of different structures in sequence-defined oligomers. The proportions of these structures could be controlled by the concentration of trimers and an acid catalyst.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Hae-Geun Jeon, Hyun Kyung Lee, Seungwon Lee, Kyu-Sung Jeong
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Organic
Han Bit Jang, Ye Rin Choi, Kyu-Sung Jeong
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Medicinal
Ji Woong Lim, Seok Kyu Kim, Seo Yun Choi, Dong Hoi Kim, Changdev G. Gadhe, Hae Nim Lee, Hyo-Ji Kim, Jina Kim, Sung Jin Cho, Hayoung Hwang, Jihye Seong, Kyu-Sung Jeong, Jae Yeol Lee, Sang Min Lim, Jae Wook Lee, Ae Nim Pae
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2018)
Article
Biochemistry & Molecular Biology
Hak Kyun Yang, Woo Seung Son, Keon Seung Lim, Gun Hee Kim, Eun Jeong Lim, Changdev G. Gadhe, Jae Yeol Lee, Kyu-Sung Jeong, Sang Min Lim, Ae Nim Pae
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
(2018)
Article
Chemistry, Applied
Hyunseok Oh, Areum Park, Kyu-Sung Jeong, Soo Bong Han, Hyuk Lee
ADVANCED SYNTHESIS & CATALYSIS
(2019)
Article
Chemistry, Medicinal
Woo Seung Son, Kyu-Sung Jeong, Sang Min Lim, Ae Nim Pae
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2019)
Article
Chemistry, Multidisciplinary
Sung Beom Seo, Seungwon Lee, Hae-Geun Jeon, Kyu-Sung Jeong
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Kyung Mog Kim, Geunmoo Song, Seungwon Lee, Hae-Geun Jeon, Woojeong Chae, Kyu-Sung Jeong
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Areum Park, Kyu-Sung Jeong, Hyuk Lee, Hyunwoo Kim
Summary: The study identified a silver(I)-mediated intramolecular oxidative C-H amination for the efficient synthesis of diverse 3-substituted indazoles, which are challenging to be synthesized by other methods of C-H aminations. Preliminary mechanistic studies suggested that the current amination proceeds via single electron transfer (SET) mediated by Ag(I) oxidant.
Article
Chemistry, Medicinal
Areum Park, Jieon Hwang, Joo-Youn Lee, Eun Ji Heo, Yoon-Ju Na, Sein Kang, Kyu-Sung Jeong, Ki Young Kim, Sang Joon Shin, Hyuk Lee
Summary: In this study, 1H-pyrazolo[3,4-b]pyridine derivatives were synthesized as DYRK1A and 1B inhibitors, among which compound 8h showed excellent inhibitory activity towards colon cancer cells and bound to DYRK1B through various interactions. The compound also exhibited strong inhibitory activities in patient-derived colon cancer organoids model and 3D spheroid assay model of SW480 and SW620.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Geunmoo Song, Kyung Mog Kim, Seungwon Lee, Kyu-Sung Jeong
Summary: Aromatic helical receptors P-1 and P-2 were modified slightly by aerobic oxidation to produce new receptors P-7 and P-8 with right-handed helical cavities, which led to significant changes in binding properties for chiral guests. Subtle post-modifications of the synthetic receptors were shown to significantly alter their binding affinities and selectivities, especially for guests with long and flexible chains.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Oncology
Jieon Hwang, Areum Park, Chinwoo Kim, Danbi Yu, Hyungju Byun, Minhee Ku, Jaemoon Yang, Tae Il Kim, Kyu-Sung Jeong, Ki Young Kim, Hyuk Lee, Sang Joon Shin
Summary: The novel inhibitor KS40008 exhibits cytotoxicity in colorectal cancer cells by inhibiting DYRK1A/B, leading to mitochondrial dysfunction and endoplasmic reticulum stress, promoting autophagic cancer cell death.
ANTICANCER RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Hye Jin Jang, Seungwon Lee, Byung Jun An, Geunmoo Song, Hae-Geun Jeon, Kyu-Sung Jeong
Summary: A new aromatic foldamer has been synthesized, featuring helical conformations stabilized by dipole-dipole interactions and pi-stacking. This foldamer has been further modified into a synthetic receptor with a tweezer-type binding cavity, in contrast to most aromatic foldamers with internal binding cavities.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Geunmoo Song, Kyu-Sung Jeong
Article
Chemistry, Organic
Chaeeun Lee, Hyemi Lee, Seungwon Lee, Hae-Geun Jeon, Kyu-Sung Jeong
ORGANIC CHEMISTRY FRONTIERS
(2019)