Article
Chemistry, Applied
Ezzat Khan
Summary: Alkenylsilanes with chlorosilyl and boryl groups attached to a carbon atom were synthesized through hydroboration of alkynylsilanes. They reacted with N-trimethylsilylpyrazole and N-2-(trimethylsilylamino)pyridine to form Si-N bonds, resulting in heterocycles containing Si, N, and B atoms. Treatment of a dichlorosilane with trimethylsilylpyrazole yielded a bis(pyrazolyl)silane.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Review
Chemistry, Medicinal
Aizhan Abdildinova, Mark J. Kurth, Young-Dae Gong
Summary: Peptidomimetics are a unique class of drug molecules, and solid-phase synthesis is an important tool for synthesizing these molecules, where small molecules including heterocycles play a key role as drug cores.
Review
Chemistry, Organic
Aizhan Abdildinova, Mark J. Kurth, Young-Dae Gong
Summary: Peptidomimetics are compounds with promising pharmacological properties that overcome limitations of peptides through backbone modifications. Accessible synthetic methodologies play a key role in peptidomimetic progress, with solid-phase organic synthesis serving as a powerful tool for their preparation. Numerous strategies for peptide backbone modifications via solid-phase synthesis have been developed in the last two decades.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Grazia Bencivenni, Diana Salazar Illera, Maria Moccia, K. N. Houk, Joseph A. Izzo, Johanna Novacek, Paolo Grieco, Mathew J. Vetticatt, Mario Waser, Mauro F. A. Adamo
Summary: Through H-1 NMR titration experiments, it was found that chiral ammonium salts interact with substrates through specific C-H positions, providing a new rationale for rationalizing the enantioselectivity in chiral phase-transfer catalysis.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Animesh Roy, Eric Koesema, Thomas Kodadek
Summary: A powerful quality control method has been developed to distinguish efficiently cyclizing scaffolds during solid-phase synthesis of thioether macrocycles without the need for tedious liquid chromatography/mass spectrometry analysis. This method can also identify linear impurities in a DNA-encoded library of macrocycles and establish a useful quality control protocol for re-synthesis of putative macrocyclic screening hits.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Ekaterina S. Sheina, Tatyana S. Shestakova, Sergey L. Deev, Igor A. Khalymbadzha, Pavel A. Slepukhin, Oleg S. Eltsov, Alexander S. Novikov, Vadim A. Shevyrin, Valery N. Charushin, Oleg N. Chupakhin
Summary: The C-N coupling of 1,2,4-triazolo[1,5-a]pyrimidin-7-ones with 1-adamantanol/1-bromoadamantane leads to the formation of 1,2,4-triazolo[4,3-a]pyrimidinium-5-olates, which are mesomeric betaines (MBs). The structures of the products were confirmed using X-ray analysis and 1D C-13 NMR spectra. Treatment of the betaines with LiHMDS resulted in the formation of anionic carbenes, which were detected using C-13 NMR spectroscopy.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Bruno Linclau, Zhong Wang, Benjamin Jeffries, Jerome Graton, Rodrigo J. Carbajo, Davy Sinnaeve, Jean-Yves Le Questel, James S. Scott, Elisabetta Chiarparin
Summary: Efficient drug discovery relies on optimizing bioactivity and compound properties such as lipophilicity, guided by efficiency metrics; the use of conformer-specific lipophilicities is a less explored strategy; optimizing lipophilicity values for different conformers can create a novel avenue in drug discovery.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Sinead McCann, William E. Roe, Hannah E. Agnew, Peter C. Knipe
Summary: To imitate the dynamic molecules in biological systems, foldamers need to possess stimulus-responsive behavior. In this study, we present a foldamer architecture based on alternating pyridine-diketopiperazine linkers. Epimerization is prevented via a copper-catalyzed coupling protocol. The native conformation of the compounds is initially investigated in both solid and solution states. The foldamers can be solubilized in DMSO and pH 9.5 buffer while retaining conformational control. Furthermore, dynamic switching is demonstrated through acid treatment, resulting in stimulus-responsive sidechain reconfiguration.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biochemistry & Molecular Biology
Marco Manenti, Simone Gusmini, Leonardo Lo Presti, Giorgio Molteni, Alessandra Silvani
Summary: Various boron-containing isocyanides were efficiently synthesized from enantiopure beta-substituted beta-amino boronic acid pinacol esters. They were used in isocyanide-based multicomponent reactions to synthesize boron-containing peptidomimetics and heteroatom-rich small molecules.
MOLECULAR DIVERSITY
(2023)
Review
Food Science & Technology
Hao-Ying-Ye Yao, Jun-Qiao Wang, Jun-Yi Yin, Shao-Ping Nie, Ming-Yong Xie
Summary: Nuclear magnetic resonance (NMR) is widely used for analyzing the molecular structure and conformation of polysaccharides. It can infer linkage and sequence of sugar residues, as well as be applied in various aspects such as conformation, quantitative analysis, and interaction analysis of polysaccharide mixtures.
FOOD RESEARCH INTERNATIONAL
(2021)
Article
Biochemistry & Molecular Biology
Svetlana A. Kondrashova, Shamil K. Latypov
Summary: The study examines the scopes and limitations of theoretical methods for estimating various NMR metrics of NHCs using computational approximations on a range of model NHCs and their derivatives. It concludes that the most reliable methods are the 31P/13C NMR shifts of NHC-phosphinidene adducts and 13C CSs of carbenes, while the method based on the analysis of 77Se CS NHC-selenoureas has some limitations due to exchange effects. The accuracy of estimating the HEP metric may also be limited due to the nonlinear effect of electron distribution. 13C CSs of NHC-azolium salts are deemed unreliable due to the influence of counterion exchange.
Article
Chemistry, Multidisciplinary
Bastian von Holtum, Maximilian Kubot, Christoph Peschel, Uta Rodehorst, Martin Winter, Sascha Nowak, Simon Wiemers-Meyer
Summary: Despite intensive research in lithium ion and lithium metal batteries, the formation of solid-electrolyte interphase (SEI) in lithium-metal-anode-based battery systems still remains a challenge. This study presents a novel approach using gas, liquid electrolyte, and solid phase accumulation to unravel the SEI compound profile. By leveraging the intrinsic reactivity of lithium metal with the liquid electrolyte, this method offers qualitative and quantitative insights into the wide range of compounds formed in carbonate-based electrolytes through state-of-the-art analytical techniques.
Article
Chemistry, Multidisciplinary
Bastian von Holtum, Maximilian Kubot, Christoph Peschel, Uta Rodehorst, Martin Winter, Sascha Nowak, Simon Wiemers-Meyer
Summary: Despite extensive research in lithium ion and lithium metal batteries, there are still unanswered questions regarding the formation of the solid-electrolyte interphase (SEI) in lithium-metal-anode-based battery systems. This study presents a novel approach that combines the intrinsic behavior of lithium metal with state-of-the-art analytical methods to unravel the compound profile of the SEI. The results reveal the vast variety of compounds formed in carbonate-based electrolytes.
Article
Chemistry, Physical
Benedikt Soeldner, Kristof Grohe, Peter Neidig, Jelena Auch, Sebastian Blach, Alexander Klein, Suresh K. Vasa, Lars V. Schaefer, Rasmus Linser
Summary: Understanding macromolecular function, interactions, and stability requires detailed assessment of conformational ensembles. Limited by the qualitative or low abundance of solid-state nuclear magnetic resonance internuclear distance information, accurately elucidating the spatial dynamics of solid proteins at physiological temperatures is challenging. However, this study demonstrates unprecedented access to abundant proton-proton internuclear distances, enabling accurate molecular dynamics simulations and providing atomic-level spatial details of conformational dynamics in various biomolecular systems.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Biochemistry & Molecular Biology
Xabier Guarrochena, Barbara Kaudela, Thomas L. Mindt
Summary: The use of 1,4-disubstituted 1,2,3-triazoles as trans-amide bond surrogates has become an important tool for the synthesis of metabolically stabilized peptidomimetics. An automated synthesis method using peptide synthesizers is described. The optimized procedure allows for the efficient synthesis of diverse triazolo-peptidomimetics with moderate to good purities.
JOURNAL OF PEPTIDE SCIENCE
(2023)
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
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, Physical
Carlos J. Moreno, Karel Hernandez, Simon J. Charnok, Samantha Gittings, Michael Bolte, Jesus Joglar, Jordi Bujons, Teodor Parella, Pere Clapes
Summary: Three enzymatic routes have been reported for the synthesis of gamma-hydroxy-alpha-amino acids through tandem aldol addition-transamination reactions. The resulting chiral molecules can be further transformed into valuable chiral alpha-amino-gamma-butyrolactones, which are important intermediates for pharmaceutical synthesis.
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)
Article
Chemistry, Physical
Carlos J. Moreno, Karel Hernandez, Samantha Gittings, Michael Bolte, Jesu's Joglar, Jordi Bujons, Teodor Parella, Pere Clapes
Summary: This study presents a tandem biocatalytic stereodivergent route for the preparation of chiral 2-hydroxy acids and 2-hydroxy-4-butyrolactone derivatives using simple and achiral starting materials. The strategy involves aldol addition reactions and subsequent reduction reactions, utilizing aldolases and ketoreductases from E. coli, Pseudomonas putida, and Pseudomonas syringae pv. tomato DSM 50315. A total of 29 structurally diverse compounds were synthesized with high enantiomeric excess and isolated yields.
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
Roser Marin-Valls, Karel Hernandez, Michael Bolte, Teodor Parella, Jesus Joglar, Jordi Bujons, Pere Clapes
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(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.
