Article
Chemistry, Multidisciplinary
Rebecca L. L. Spicer, Curtis C. C. Shearman, Nicholas H. H. Evans
Summary: This study presents the synthesis of two mechanically chiral rotaxanes with urea and squaramide motifs, with yields of 33% and 22% respectively. H-1 NMR spectroscopic titrations reveal the possibility of shuttling the macrocycle, detectable through modulation of mechanical chirality expression in the NMR spectrum, by the addition of achiral chloride anions, which can be reversed by the addition of sodium cations.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Daniel Kohs, Jonathan Becker, Hermann A. Wegner
Summary: In this study, a modular synthesis method was reported for the preparation of substituted cycloparaphenylenes (CPPs) of different sizes. By using a specific compound, the ring size of the final product can be conveniently controlled. Substituted nanohoops were successfully synthesized through a simple reaction and exhibited a tightly packed tube-like arrangement in the crystal structure.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Fabian M. Steudel, Ernest Ubasart, Luigi Leanza, Miriam Pujals, Teodor Parella, Giovanni M. Pavan, Xavi Ribas, Max von Delius
Summary: This study demonstrates the successful synthesis of a challenging task by adding two unsymmetric malonate esters to Buckminster fullerene C60, resulting in 22 spectroscopically distinguishable isomeric products. By combining three different approaches, namely tether approach, template approach, and shadow mask approach, the researchers achieved 87% selectivity for the formation of a single isomer.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Isabel Lopez-Martin, Jacobo Veiga-Herrero, Fatima Aparicio, David Gonzalez-Rodriguez
Summary: We describe an optimized design and modular synthetic approach for the formation of discrete macrocyclic species of controllable size and shape through amidinium-carboxylate interactions in both apolar and polar media.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Yuezhou Liu, Hongliang Wang, Peiren Liu, Huangtianzhi Zhu, Bingbing Shi, Xin Hong, Feihe Huang
Summary: A series of azo-based macrocyclic arenes were designed and synthesized, showing changes in cavity size upon photoisomerization and successful light-controlled host-guest complexation. This work provides a simple and effective method for preparing azo-macrocycles and may further advance the design and applications of novel photo-responsive host-guest systems.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Mathias Hermann, Daniel Wassy, Julia Kohn, Philipp Seitz, Martin U. Betschart, Stefan Grimme, Birgit Esser
Summary: Conjugated nanohoops exhibit unexpected optoelectronic properties and chirality, with bending of the pi-system leading to the synthesis of chiral hoops. By incorporating dibenzo[a,e]pentalenes and using a bent diketone unit, chiral conjugated nanohoops were stereoselectively synthesized with small HOMO-LUMO gap and ambipolar electrochemical character. The chiral hoop showed stability even at high temperatures and was capable of accommodating two C60 molecules, as indicated by binding studies.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jonathan Pfeuffer-Rooschuez, Salome Heim, Alessandro Prescimone, Konrad Tiefenbacher
Summary: This study reports the synthesis of a novel structural platform suitable for constructing megalo-cavitands with large volumes. These megalo-cavitands selectively bind to C-60 and C-70.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Kui Wang, Guo-Jie Gao, Xiao-Yan Wang
Summary: The study successfully lowered the critical micelle concentration of congo red by the host-guest interactions between calixpyridinium and anionic bola surfactants, resulting in a valuable visible-light response for the complete photodegradation of congo red.
JOURNAL OF MOLECULAR LIQUIDS
(2021)
Article
Chemistry, Organic
Rajdip Chowdhury, Gabor Zoltan Elek, Beatriz Meana-Baamonde, Abraham Mendoza
Summary: (Borylmethyl)trimethylsilanes are important building blocks with unique reactivity in organic synthesis. However, the synthesis of more advanced derivatives is limited due to the requirement of advanced silicon intermediates. This study develops a one-pot synthesis of (borylmethyl)silanes using available alkyl, aryl, alkoxy, aryloxy, and silyl-hydrosilane materials. The reactivity of N-hydroxyphthalimidyl diazoacetate (NHPI-DA) in Si-H insertion and alpha-silyl redox-active esters in different decarboxylative borylation reactions is investigated.
Article
Chemistry, Physical
Laicheng Zhou, Ran He, Yang Qin, Yi-Lin Wu, Li Jiang, Dong-Dong Zhou, Ling Zhang
Summary: In this study, a strategy for directed self-assembly based on C-H/N-H...anion hydrogen bond enhanced pi-pi interactions in water was reported, allowing for precise control of surface charge distance in nanosheets, with potential applications in capturing DNA.
Article
Engineering, Biomedical
Liang Zhao, Junyi Chen, Long Tian, Yahan Zhang, Longming Chen, Xinbei Du, Mengke Ma, Jian Li, Qingbin Meng, Chunju Li
Summary: This study introduces a novel detoxification method for macromolecular biotoxins using a large macrocycle. The complexation between the macrocycle and a peptide biotoxin reduces its cytotoxicity and shows therapeutic effects in poisoned mice.
ADVANCED HEALTHCARE MATERIALS
(2022)
Article
Chemistry, Multidisciplinary
Donglei Wang, Ying-Bo Shao, Yunrong Chen, Xiao-Song Xue, Xiaoyu Yang
Summary: An efficient method for the asymmetric synthesis of planar-chiral macrocycles (paracyclophanes) has been developed using chiral phosphoric acid catalysis for enantioselective electrophilic aromatic aminations with azodicarboxylates. This method allows for the synthesis of a wide range of chiral macrocycles with varying ring sizes and functional groups, achieving high yields and enantioselectivities. The mechanism and origins of the stereoselectivities of these reactions were investigated through experimental studies and computational calculations. Preliminary utilization of the planar-chiral macrocycle as a chiral organocatalyst demonstrated the potential applications of these novel chiral skeletons.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Annie R. Hooper, Andraz Ostrek, Ana Milian-Lopez, David Sarlah
Summary: This study presents a chemical synthesis method for preparing pyritide A2, involving the synthesis of a pyridine ring from an amino acid precursor, resulting in the efficient preparation of this class of natural products and analogues.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Karolis Norvaisa, Kathryn Yeow, Brendan Twamley, Marie Roucan, Mathias O. Senge
Summary: This study explores the benefits of combining nonplanar porphyrins with traditional molecular designs to introduce new concepts. Selective demethylation based on less hindered positions, isolation of symmetrical and unsymmetrical porphyrin compounds, and analyzing intramolecular interactions via X-ray crystallography highlight the importance of nonplanar systems in supramolecular ensemble design.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Si-Qi Chen, Wei Zhao, Biao Wu
Summary: The proper concentration of sulfate anion is essential for key physiological functions, and recent research on sulfate recognition and separation has made progress, with molecular recognition being the key element for selective sulfate separations.
FRONTIERS IN CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Ignacio Alfonso, Jordi Sola
CHEMISTRY-AN ASIAN JOURNAL
(2020)
Article
Chemistry, Physical
Ahmed H. Lotfallah, M. Isabel Burguete, Ignacio Alfonso, Santiago Luis
JOURNAL OF COLLOID AND INTERFACE SCIENCE
(2020)
Article
Multidisciplinary Sciences
Demetrio Raldua, Marta Casado, Eva Prats, Melissa Faria, Francesc Puig-Castellv, Yolanda Perez, Ignacio Alfonso, Chuan-Yu Hsu, Mark A. Arick, Natalia Garcia-Reyero, Tamar Ziv, Shani Ben-Lulu, Arie Admon, Benjamin Pina
SCIENTIFIC REPORTS
(2020)
Article
Chemistry, Multidisciplinary
Daniel Carbajo, Yolanda Perez, Jordi Bujons, Ignacio Alfonso
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Biochemical Research Methods
Yolanda Perez, Marta Casado, Demetrio Raldua, Eva Prats, Benjamin Pina, Roma Tauler, Ignacio Alfonso, Francesc Puig-Castellvi
ANALYTICAL AND BIOANALYTICAL CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Jacobo Gomez-Gonzalez, Yolanda Perez, Giuseppe Sciortino, Lorena Roldan-Martin, Jose Martinez-Costas, Jean-Didier Marechal, Ignacio Alfonso, Miguel Vazquez Lopez, M. Eugenio Vazquez
Summary: This study introduces new artificial peptide ligands that fold into chiral helicates in the presence of labile metal ions, and demonstrates their selective binding to DNA three-way junctions as well as their internalization and staining capabilities in functional cells. Circular dichroism, NMR spectroscopy, and computational methods were used to identify and determine the structure of the peptide ligands as topological isomers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Lucia Tapia, Naiara Solozabal, Jordi Sola, Yolanda Perez, W. Todd Miller, Ignacio Alfonso
Summary: The study introduces a new approach to selectively protect tyrosine residues in peptides from phosphorylation by the Src TK enzyme using pseudopeptidic cages. Fluorescence emission titrations indicate that the most efficient cage inhibitors strongly bind peptide substrates, with a good correlation between binding constant and inhibitory potency. Further experimental evidence supports the proposed mechanism of selectively protecting substrates through supramolecular interactions, showcasing the potential of supramolecular complexes for modulating TK signaling.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Medicinal
Yolanda Perez, Roman Bonet, Miriam Corredor, Cecilia Domingo, Alejandra Moure, Angel Messeguer, Jordi Bujons, Ignacio Alfonso
Summary: Semaphorin 3A (Sema3A) is a cell-secreted protein involved in axonal guidance pathways, with the interaction between Sema3A and glycosaminoglycans (GAGs) taking place at the Sema3A C-terminal polybasic region. Biophysical techniques revealed that the Sema3A C-terminal region is intrinsically disordered, with studies showing that a new peptoid molecule may disrupt the interaction between the C-terminal region and heparin, opening up potential therapeutic applications targeting protein-GAG interactions.
Article
Chemistry, Medicinal
Daniel Carbajo, Yolanda Perez, Marta Guerra-Rebollo, Eva Prats, Jordi Bujons, Ignacio Alfonso
Summary: Dynamic combinatorial chemistry is used to optimize heparin binders with submicromolar affinity. The interaction between these binders and heparin is studied using various experimental and theoretical approaches, and the potential use of these binders as heparin reversal drugs is demonstrated in ex vivo and in vivo assays.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Alba Sors-Vendrell, Albert Ortiz, Diego Meneses, Ignacio Alfonso, Jordi Sola, Ciril Jimeno
Summary: This study utilizes a new catalytic system that increases the probability and rate of the asymmetric aldol reaction, and achieves a remarkable decrease in catalyst loading to 2 mol %.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Organic
Lucia Tapia, Ignacio Alfonso, Jordi Sola
Summary: Artificial receptors that can recognize biological molecules or ions have attracted interest in the chemical community. Molecular cages are polycyclic compounds designed to encapsulate guest species. Despite challenges in their chemical preparation, molecular cages have great potential for applications such as sensing, delivery, and purification.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Daniel Carbajo, Antonio Jesus Ruiz-Sanchez, Francisco Najera, Ezequiel Perez-Inestrosa, Ignacio Alfonso
Summary: The spontaneous [2+2] macrocyclization of tetrakis(aminals) shows unexpected stability, structural modularity, dynamic connections, and water tolerance, making them attractive systems for future applications as stimulus-responsive materials.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Jordi Sola, Ciril Jimeno, Ignacio Alfonso
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Rosa Marti-Centelles, Jenifer Rubio-Magnieto, Beatriu Escuder
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Analytical
Lucia Tapia, Yolanda Perez, Jordi Sola, Santiago V. Luis, Ignacio Alfonso, Cristian Vicent
Summary: The interaction between the EYE tripeptide and pseudopeptidic cages was thoroughly investigated using various analytical techniques to determine their stoichiometry and affinities in aqueous and gas-phase environments. The binding of EYE was found to be influenced by the side chains of the cages, with cages bearing basic groups showing tighter binding in aqueous media.