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
Chemistry, Multidisciplinary
Oscar Francesconi, Francesco Milanesi, Cristina Nativi, Stefano Roelens
Summary: In designing new biomimetic receptors for carbohydrates, shape-persistent macrocyclic structures are commonly chosen for effective recognition of neutral saccharides in water. However, this study found that acyclic receptors, while less explored, provide advantages in terms of selectivity for recognizing important 1,4-disaccharides in biological contexts. NMR spectroscopic data and molecular modeling calculations were used to analyze the differences in binding mode and shed light on the origin of recognition efficacy and selectivity.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Canjia Zhai, Chengkai Xu, Yunpeng Cui, Lukasz Wojtas, Wenqi Liu
Summary: A biomimetic receptor with high affinity and selectivity for glucose has been synthesized using dynamic imine chemistry. The receptor features two durene panels and two pyridinium residues, which enhance solubility and provide polarized C-H bonds for substrate binding. These findings demonstrate the potential of dynamic covalent chemistry for creating molecular receptors and advancing carbohydrate recognition in water.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Douglas H. Banning, Grace M. Kuhl, Madeline M. Howell, Darren W. Johnson
Summary: In this study, ChemFETs were used to evaluate the anion affinity of two different supramolecular scaffolds, showing that receptor modification can impact chemical selectivity. Slight changes in the steric bulk of the supramolecular scaffolds resulted in orders of magnitude differences in aqueous anion detection limits of ChemFET sensors.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Khushabu Thakur, Milan A. Shlain, Mateusz Marianski, Adam B. Braunschweig
Summary: Synthetic carbohydrate receptors have potential applications in disease detection, drug delivery, and modification of complex carbohydrates, but challenges exist in binding affinity and substrate selectivity. By studying flexible SCRs based on a biaryl core with heterocyclic groups, it was found that the role of heterocycles is crucial in determining substrate selectivity, leading to the development of design rules for all SCRs in this class.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Dharmendra Singh, Durga Lakshmi, Chhuttan L. Meena, Gamidi Rama Krishna, Gangadhar J. Sanjayan
Summary: This paper reports on the development of carbamate-protected 2-aminopyrimidinedione-based Janus G-C nucleobases as building blocks for smart polymers and self-healing materials. These nucleobases feature polymerizable groups and self-complementary triple H-bonding motifs, enabling the synthesis of smart polymers and eliminating solubility issues.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Bryce da Camara, Connor Z. Woods, Komal Sharma, Hoi-Ting Wu, Naira S. Farooqi, Changwei Chen, Ryan R. Julian, Douglas A. Vander Griend, Richard J. Hooley
Summary: Spacious M4L6 tetrahedra can act as catalytic inhibitors for base-mediated reactions by increasing the acidity of the reaction solvent, resulting in a reduced conversion rate of the conjugate addition reaction.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Physical
Xander Schaapkens, Joel H. Holdener, Jens Tolboom, Eduard O. Bobylev, Joost N. H. Reek, Tiddo J. Mooibroek
Summary: Designing compounds for the selective molecular recognition of carbohydrates is a challenging task for supramolecular chemists. Macrocyclic compounds incorporating isophtalamide or bisurea spacers have proven effective for selective recognition of all-equatorial carbohydrates. The octa-urea [Pd2L4](4+) cage complex shows excellent selectivity towards n-octyl-alpha-D-Mannoside with inhibited binding of n-octyl glycosides by small anions like NO3- and BF4-.
Article
Chemistry, Multidisciplinary
Daniel A. Decato, Asia Marie S. Riel, James H. May, Vyacheslav S. Bryantsev, Orion B. Berryman
Summary: This paper experimentally quantifies a Hydrogen Bond-Enhanced Halogen Bond (HBeXB) for the first time, showing that electron-rich halogen bond donors are strengthened most by an adjacent hydrogen bond, and stronger hydrogen bond donors enhance the halogen bond the most. X-ray crystal structures and F-19 NMR titrations support the findings, laying the foundation for future studies on hydrogen bonds and halogen bonds in close proximity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Jinqiao Dong, Anthony P. Davis
Summary: Hydrogen bonding plays a key role in molecular recognition, and recent research has focused on utilizing it in water. Synthetic receptors combining hydrogen bonding with hydrophobic interactions show promise for biomedical applications in the future.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Chi-Huao Huang, Damien Jardel, Guillaume Lautrette, Isabelle Pianet, Alexander Kuhn, Dario M. Bassani
Summary: A series of receptors with H-bonding sites complementary to barbituric acid are used to induce the assembly of ladder-like structures containing triphenylenevinylene units appended with barbituric acid. Through-space interactions between electroactive moieties in the assemblies are enforced by the topological constraints of the architectures, leading to the formation of radical cation species with delocalized charges.
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, Physical
Filip Perlitius, Anna Walczak, Miroslava Conkova, Grzegorz Markiewicz, Jack Harrowfield, Artur R. Stefankiewicz
Summary: This study investigates the non-covalent aggregation of four benzene-1,3,5-tricarboxamide (BTA) derivatives formed from glycine or L-valine esters in both solid-state and chloroform solution. The study reveals the significant role of the steric bulk of the C-terminus protecting group in supramolecular aggregation in the solid-state and highlights the essential influence of substituent steric bulk on the nature and stability of BTA aggregates in distinct phases.
JOURNAL OF MOLECULAR LIQUIDS
(2022)
Article
Materials Science, Multidisciplinary
Elisa Calabrese, Liberata Guadagno, Marialuigia Raimondo, Andrea Sorrentino, Simona Russo, Pasquale Longo, Annaluisa Mariconda
Summary: This study reports the synthesis and characterization of PEGMA-based copolymers incorporating different percentages of HEMA-UPy and evaluates their thermal properties and healing efficiency. The results show that increasing the amount of HEMA-UPy moiety leads to slight changes in glass transition temperature and significant changes in crystallization and melting temperatures. Dynamic mechanical analysis demonstrates the ability of the copolymer to recover its original storage modulus values.
MACROMOLECULAR MATERIALS AND ENGINEERING
(2023)
Article
Chemistry, Multidisciplinary
Stephanie A. Boer, Luke Conte, Andrew Tarzia, Michael T. Huxley, Michael G. Gardiner, Dominique R. T. Appadoo, Courtney Ennis, Christian J. Doonan, Christopher Richardson, Nicholas G. White
Summary: Three isoreticular hydrogen bonded organic frameworks assembled through charge-assisted amidinium center dot center dot center dot carboxylate hydrogen bonds were studied, revealing extreme yet recoverable molecular-level framework reorganization during phase transitions. The water content was found to control the transformations, and the non-porous anhydrous phase showed reversible water sorption through crystal restructuring.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)