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
Biochemistry & Molecular Biology
Amila M. Abeysekera, Abhijeet S. Sinha, Christer B. Aakeroy
Summary: Strategies for co-crystal synthesis typically involve hydrogen- or halogen-bond interactions, but predicting the structural influence of both simultaneously can be challenging. Experimental co-crystallization of aliphatic dicarboxylic acids with various target molecules revealed that the structural impact of halogen atoms increases with size, with the abilities of Cl < Br < I in forming sigma-holes.
Article
Chemistry, Multidisciplinary
Chenxiao Qian, Pengfei Li, Jianwei Sun
Summary: A catalytic enantioselective variant of oxidative rearrangement of indoles to access oxindoles has been developed using chiral phosphoric acid catalysis, providing a rapid access to a range of enantioenriched spirooxindoles with high enantioselectivity controlled by dynamic kinetic resolution.
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, 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, Physical
Liya Dai, Pengyao Xing, Aiyou Hao
Summary: In this study, the aryl-group achiral molecular tweezers were found to effectively include chiral guest molecules via halogen bonding and other noncovalent interactions. Experimental and computational calculations revealed the formation of stable 1:1 host-guest complexes, demonstrating the transfer of chirality to achiral host molecules at the supramolecular level.
JOURNAL OF PHYSICAL CHEMISTRY C
(2023)
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, Multidisciplinary
Chang-Qiu Guo, Chuan-Jun Lu, Li-Wen Zhan, Peng Zhang, Qi Xu, Jia Feng, Ren-Rong Liu
Summary: This study reports a new catalyst that successfully catalyzes the enantioselective coupling reaction between quinone esters and anilines, resulting in the formation of N-aryl quinone atropisomers with a unique intramolecular hydrogen bond. This method has the potential to be used for the synthesis of structurally diverse secondary amine atropisomers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Shohei Tashiro, Kosuke Nakata, Ryunosuke Hayashi, Mitsuhiko Shionoya
Summary: This paper demonstrates the molecular recognition of amino acid and peptide derivatives by multipoint hydrogen bonding in a porous metal-macrocycle framework revealed by single-crystal X-ray diffraction analysis. l-Serine residues are site-selectively and residue-specifically adsorbed on the pore surface via multiple hydrogen bonds. A serine derivative is diastereoselectively recognized on the (P)- or (M)-side of the enantiomeric pore surface, and the conformation of the peptide is highly regulated, incorporating a poly-L-proline type I helix-like structure into the pore.
Article
Chemistry, Multidisciplinary
Tao Yuan, Weiwei Gao, Qiaochun Wang
Summary: A new method was developed to synthesize the cage-like sulfuryl-bridged triazinane molecule HEXS with a relatively high yield of 64%. HEXS selectively binds to SO42- with a high binding constant through multiple C-H...O hydrogen bonding interactions.
RESEARCH ON CHEMICAL INTERMEDIATES
(2022)
Article
Chemistry, Organic
Catherine Fressigne, Alexandre Jean, Morgane Sanselme, Jerome Blanchet, Jacques Rouden, Jacques Maddaluno, Michael De Paolis
Summary: Cation-pi interactions between various onium salts, alkynes, and acetylene were studied, taking into account the substituents of the triple bond, the nature of the anions, and the polarity of the solvent. The stability of folded conformers of alkynyl onium salts, even substituted with electron-withdrawing groups, was confirmed through MP2 calculations and experiments. Thorough in silico studies using natural bonding orbital analysis were carried out to examine the contribution of these interactions on the alkyne electronic population. The results highlighted the intramolecular interactions from sulfonium salt tethered to phenylalkyne and high energy interactions of acetylene or phenylacetylene with phenyldimethylsulfonium chloride.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jose J. Garrido-Gonzalez, Irene Boya del Teso, Angel L. Fuentes de Arriba, Francisca Sanz, Eva M. Martin del Valle, Joaquin R. Moran, Victoria Alcazar
Summary: Cleft type receptors with the oxyanion hole motif were synthesized straightforwardly from commercial starting materials. These receptors showed the ability to adjust to different guests by combining hydrogen bonds and charge-transfer interactions, leading to further stabilization of the complexes. Modeling studies and bidimensional NMR experiments were conducted to provide additional information on these complexes.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Rosa Lopez, Claudio Palomo
Summary: N,N-Diacylaminals are flexible molecular scaffolds commonly used as amide surrogates in peptidomimetics. Recently, their singularity as an N-acyl imine equivalent and hydrogen-bond donor has led to new synthetic opportunities, particularly in the field of asymmetric catalysis. This concept article highlights the diverse synthetic potential of N,N-Diacylaminals and provides the necessary elements for further developments.
CHEMISTRY-A EUROPEAN JOURNAL
(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
Hisashi Hashimoto, Yoshihiro Ueda, Kiyosei Takasu, Takeo Kawabata
Summary: Catalyst-controlled substrate-selective silylation of alcohols is achieved independently of the reactivity of hydroxy group based on steric environment. The reaction shows high selectivity towards 1,5-amino alcohol derivatives and discriminating ability towards remote functionality at C(5) from reacting hydroxy groups in the silylation of pentanol analogues.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
