Article
Chemistry, Applied
Ravindra S. Phatake, Noy B. Nechmad, Ofer Reany, N. Gabriel Lemcoff
Summary: A selective ring-closing metathesis (RCM) reaction using latent sulfur chelated ruthenium iodide benzylidenes as catalysts, activated by thermal and photochemical stimuli, has been reported. This method enables the formation of large macrocycles with high yields, especially for dienes with one terminal alkene and one internal double bond. For substrates containing two internal double bonds, a sacrificial methylene donor can be used to obtain the desired products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Adrian Sytniczuk, Mariusz Milewski, Michal Dabrowski, Karol Grela, Anna Kajetanowicz
Summary: A set of macrocyclic unsaturated musk compounds were obtained through a high-concentration RCM process, achieved by forming oligomers and then undergoing backbiting metathesis reaction. The process exhibited high selectivity and yielded pure macrocyclic musk products. The reaction conditions were user-friendly and environmentally friendly, using commercially available catalyst and bio-sourced oleic acid substrates.
Article
Chemistry, Multidisciplinary
Yucheng Mu, Felix W. W. Hartrampf, Elsie C. Yu, Katherine E. Lounsbury, Richard R. Schrock, Filippo Romiti, Amir H. Hoveyda
Summary: This study introduces a new method for synthesizing trisubstituted macrocyclic olefins, which can produce stereoisomers and overcome unexpected difficulties. The effectiveness of the method is demonstrated through two examples.
Article
Chemistry, Organic
Atsushi Ueda, Yui Makura, Sana Kakazu, Takuma Kato, Tomohiro Umeno, Kazuhiro Hirayama, Mitsunobu Doi, Makoto Oba, Masakazu Tanaka
Summary: In this study, a selective E-type ring-closing metathesis reaction was discovered in α-helical stapled peptides. By using chiral carbocyclic α,α-disubstituted α-amino acids, a high E-selectivity was achieved, while standard acyclic amino acids resulted in lower selectivity. The stapled octapeptide exhibited a right-handed α-helical crystal structure.
Article
Chemistry, Physical
Charles Killeen, Jie Liu, Harmen S. S. Zijlstra, Florian Maass, James Piers, Reid Adams, Allen Oliver, J. Scott McIndoe
Summary: Ring-closing metathesis (RCM) is a versatile method for forming cyclic structural elements. Real-time analysis using electrospray ionization mass spectrometry (ESI-MS) was applied to study the RCM reaction, revealing the presence of by-products and the decomposition of the catalyst. Isomerization reactions play a significant role in affecting the yield of the desired product, especially in slow RCM reactions.
CATALYSIS SCIENCE & TECHNOLOGY
(2023)
Article
Chemistry, Organic
Damien F. Dewez, Christina Diacofotaki, Gwilherm Evano
Summary: A new class of nitrogen-containing heterocycles featuring both a cyanamide and an unsaturated ring can be readily obtained through ring-closing metathesis. These compounds have potential applications in drug discovery and can serve as building blocks. The presence of the endocyclic double bond provides a useful access to novel polycyclic heterocycles.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Anas Semghouli, Attila M. Remete, Lorand Kiss
Summary: Novel functionalized fused-ring β-amino lactones and lactams with multiple chiral centers were synthesized from readily available strained bicyclic β-amino acids via a stereocontrolled synthetic route. The key step involved ring-rearrangement metathesis of allyl/propargyl esters or N-allylated/N-propargylated amides of (oxa)norbornene β-amino acids. The RRM transformations were investigated using commercially available catalysts. Importantly, the procedure did not alter the configurations of the chiral centers, meaning that the starting (oxa)norbornene β-amino acids predetermined the configuration of the formed products.
Article
Chemistry, Multidisciplinary
Wensen Chen, Changjuan Guo, Hao Ding, Xingyu Yang, Ke Zhang
Summary: A novel controlled ring-opening polymerization method has been developed using a trimethyl lock unit as a ring-opening trigger, which enables the synthesis of polymers with controlled molecular weights and narrow dispersities. This versatile method can be applied to the synthesis of various polymers with different functionalities and structures.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Polymer Science
Brad H. Jones, Chad Staiger, Jackson Powers, Jeremy A. Herman, Jessica Roman-Kustas
Summary: This study introduces a novel series of linear and crosslinked polyurethanes, along with a selective depolymerization method under mild conditions. By utilizing unique polyols and specific synthesis techniques, the polymer chain can be cleaved in a controlled manner, allowing for the development of recyclable materials with potential for further re-polymerization.
MACROMOLECULAR RAPID COMMUNICATIONS
(2021)
Article
Chemistry, Inorganic & Nuclear
Alexander Kaps, Sabine Foro, Herbert Plenio
Summary: Three different types of bimetallic NHC-metal complexes were synthesized, and their properties were investigated. The complexes were based on xanthene and various metals were used as the ML units.
DALTON TRANSACTIONS
(2022)
Review
Chemistry, Organic
Santhosh Kumar Podiyanachari, Hassan S. Bazzi, Mohammed Al-Hashimi
Summary: Synthesis of cycloolefin-based polymers via metathesis-accompanied cyclopolymerization and tandem ring-opening/ring-closing metathesis (RO/RCM) polymerization leads to highly functional cycloolefin ring-based polymers.
CURRENT ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Phong K. Quach, Jesse H. Hsu, Ivan Keresztes, Brett P. Fors, Tristan H. Lambert
Summary: The ring-opening metathesis polymerization of cyclopropenes using hydrazonium initiators was investigated. The initiators, formed by condensing 2,3-diazabicyclo[2.2.2]octane and an aldehyde, polymerize cyclopropene monomers through a sequence of [3+2] cycloaddition and cycloreversion reactions. The study showed that the monomer to initiator ratio had a positive correlation with the degree of polymerization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Plant Sciences
Jiahui Lin, Zihao Zhu, Yuwen Chen, Weiwei Zuo, Meifang Zhu, Zhiyuan Ma
Summary: The combination of ring-closing metathesis with betulin allows for the synthesis of a library of triterpenoid derivatives for potential pharmacological research. Different types of betulin derivatives were prepared by coupling reactions and subsequent ring-closing metathesis. The resulting betulin-based olefin derivatives showed potential applications in the biomedical field.
JOURNAL OF NATURAL PRODUCTS
(2023)
Article
Chemistry, Multidisciplinary
Wioletta Kosnik, Dawid Lichosyt, Marcin Sniezek, Angelika Janaszkiewicz, Krzysztof Wozniak, Maura Malinska, Bartosz Trzaskowski, Anna Kajetanowicz, Karol Grela
Summary: The formation of sterically hindered C-C double bonds through catalytic olefin metathesis is a challenging task for Ru catalysts. To overcome this limitation, a new NHC ligand was designed, which reduced the susceptibility of small-size NHC catalysts to decomposition. The resulting isomeric complexes exhibited similar high thermodynamic stability but different application profiles in catalysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Polymer Science
Mohammad Yasir, Andreas F. M. Kilbinger
Summary: Norbornene and cyclohexene show different polymerization behaviors using Grubbs' catalysts due to their varying ring strain energy levels; a sequence-selective cascade polymerization of a monomer containing both rings resulted in polymers with moderate molecular weight dispersities and good control over molecular weight.
Article
Chemistry, Multidisciplinary
Lotta Turunen, Flora Boroka Nemeth, Daniel A. Decato, Imre Papai, Orion B. Berryman, Mate Erdelyi
Summary: The distinct difference between the three-center halogen bond and the analogous three-center coordinative bond of silver is demonstrated through computational, X-ray crystallographic, and solution NMR spectroscopic investigations of their complexes with a bidentate Lewis base. Iodine(I) tends to form entropically favored monomeric complexes, while silver(I) forms enthalpically favored dimeric complexes. The structure of the silver complexes is significantly influenced by counterion coordination in both solution and solid state, in contrast to the minimal effect it has on the analogous halogen bond.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2021)
Article
Chemistry, Multidisciplinary
Lianne H. E. Wieske, Mate Erdelyi
Summary: Most NMR-based 3-D structure determinations rely on NOESY spectra to utilize NOE, but the use of NUS to accelerate the process may lead to decreased accuracy and loss of long-range correlations. Weak NOE signals are more severely affected by NUS, resulting in increased errors in NOE-based distance measurements.
MAGNETIC RESONANCE IN CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Yoseph Atilaw, Vasanthanathan Poongavanam, Caroline Svensson Nilsson, Duy Nguyen, Anja Giese, Daniel Meibom, Mate Erdelyi, Jan Kihlberg
Summary: PROTACs induce intracellular degradation of target proteins through a bifunctional structure. Structural insights into a VHL-based PROTAC revealed elongated and polar conformations in solutions, suggesting the importance of molecular chameleonicity for cell permeability.
ACS MEDICINAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Medicinal
Carolyne Chepkirui, Purity J. Ochieng, Biswajyoti Sarkar, Aabid Hussain, Chiranjib Pal, Li Jun Yang, Paolo Coghi, Hoseah M. Akala, Solomon Derese, Albert Ndakala, Matthias Heydenreich, Vincent K. W. Wong, Mate Erdelyi, Abiy Yenesew
Summary: Five compounds were isolated from the leaves of Mundulea sericea, with three additional compounds isolated from the roots. Compound 1 showed good antiplasmodial activity, while compounds 2 and 5 exhibited activity against drug-sensitive Leishmania donovani. Compound 3 showed significant cytotoxicity against human cell lines, while the other compounds displayed low cytotoxicity.
Editorial Material
Chemistry, Multidisciplinary
Mate Erdelyi, Catharine Esterhuysen, Weiliang Zhu
Article
Chemistry, Multidisciplinary
Stefan Peintner, Mate Erdelyi
Summary: This study introduces a strategy for accurate experimental description of weak chemical forces in solution, demonstrating its scope and effectiveness through experiments. The methodology utilizes entropic advantage and ensemble analysis to describe the orientation of weak force interactions, and derives thermodynamic constants through temperature-dependent chemical shift analysis.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Maria Quant, Andreas Erbs Hillers-Bendtsen, Shima Ghasemi, Mate Erdelyi, Zhihang Wang, Lidiya M. Muhammad, Nina Kann, Kurt Mikkelsen, Kasper Moth-Poulsen
Summary: This study presents a novel cross-coupling reaction strategy for the efficient synthesis of a series of new BOD compounds, capable of reversible transformation into TCOs with minimal degradation over multiple cycles. Computational and experimental findings demonstrate the potential for designing future BOD/TCO systems with tailored properties, showing higher storage energies compared to norbornadiene.
Article
Chemistry, Medicinal
Lianne H. E. Wieske, Jonathan Bogaerts, Albin A. M. Leding, Scott Wilcox, Anna Andersson Rasmussen, Kinga Leszczak, Lotta Turunen, Wouter A. Herrebout, Madlen Hubert, Annette Bayer, Mate Erdelyi
Summary: Carbapenem resistance caused by metallo-beta-lactamases is a serious global challenge. In this study, the backbone NMR resonance assignment of VIM-2 was disclosed, providing possibilities for studying this important enzyme and its potential inhibitors.
ACS MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Katarzyna Palica, Manuela Voracova, Susann Skagseth, Anna Andersson Rasmussen, Lisa Allander, Madlen Hubert, Linus Sandegren, Hanna-Kirstirep Schroder Leiros, Hanna Andersson, Mate Erdelyi
Summary: Infectious diseases remain a major concern for public health in the 21st century, and the development of antimicrobial resistance by microbes is a significant problem. The study found that phosphonamidate compounds have the potential to become a new generation of antibiotic therapeutics to combat metallo-beta-lactamase-resistant bacteria.
Article
Chemistry, Medicinal
Gasper Maeda, Pieter J. Gilissen, Catarina Bourgard, Jelle van der Wal, Joan J. E. Munissi, Stephen S. Nyandoro, Mate Erdelyi
Summary: Several compounds were isolated from the leaves of Uvaria pandensis Verdc., showing antibacterial and cytotoxic activities.
Article
Chemistry, Multidisciplinary
Scott Wilcox, Daniel Sethio, Jas S. Ward, Antonio Frontera, Roland Lindh, Kari Rissanen, Mate Erdelyi
Summary: The interaction between a [bis(pyridine)iodine(i)](+) cation and a [bis(pyridine)silver(i)](+) cation, where an iodonium ion acts as a nucleophile by transferring electron density to the silver(i) cation, is reinvestigated in this study. No measurable interaction is observed between the cationic species in solution using NMR. DFT calculations suggest that any attractive interaction between these complexes in solution is primarily due to the pi-pi interaction of pyridines.
CHEMICAL COMMUNICATIONS
(2022)
Meeting Abstract
Biophysics
Thi Dung Nguyen, Robert Raddi, Mate Erdelyi, Vincent Voelz
BIOPHYSICAL JOURNAL
(2022)
Article
Chemistry, Inorganic & Nuclear
Ann Christin Reiersolmoen, Stefano Battaglia, Andreas Orthaber, Roland Lindh, Mate Erdelyi, Anne Fiksdahl
Summary: A new method has been introduced to generate P,N-chelated gold(III) complexes, avoiding phosphorus ligand oxidation and demonstrating catalytic activity in the synthesis of complex molecules.
INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jonathan Bogaerts, Yoseph Atilaw, Stefan Peintner, Roy Aerts, Jan Kihlberg, Christian Johannessen, Mate Erdelyi
Summary: Understanding the conformational preferences of free ligands in solution is crucial for rationalizing structure-activity relationships in drug discovery. This study demonstrates differences in conformational behavior between two compounds and shows that the most potent compound has a conformation present in aqueous solution. Molecular Dynamics simulations produce ensembles including important conformations, but identifying relevant conformations from the large pool remains challenging. The study emphasizes the importance of understanding the scope and limitations of available techniques for conformational analyses.
Article
Chemistry, Multidisciplinary
Stefan Peintner, Mate Erdelyi
Summary: This article presents a strategy for accurately describing weak chemical forces in solution, demonstrating the geometric and thermodynamic characterization of the weak halogen bond. By using a combination of NOE- and RDC-based ensemble analyses, this methodology allows for the precise orientation of donor and acceptor sites to be determined, paving the way for improved understanding and strategic use of weak forces in chemistry and biology.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)