Synthesis of novel acridino- and phenazino-18-crown-6 ligands and their optically pure dimethyl-substituted analogues for molecular recognition studies

Tetrahedron ◽  
1999 ◽  
Vol 55 (5) ◽  
pp. 1491-1504 ◽  
Author(s):  
Péter Huszthy ◽  
Erika Samu ◽  
Borbála Vermes ◽  
Gabriella Mezey-Vándor ◽  
Mihály Nógrádi ◽  
...  
Keyword(s):  
Molecular Recognition ◽  
Optically Pure

Optically pure 2-(quinolin-8-yloxy)cyclohexan-1-ol as a practical agent for molecular recognition by NMR and fluorescence spectroscopy

2018 ◽  
Vol 54 (78) ◽  
pp. 11037-11040 ◽  
Author(s):  
Aditya N. Khanvilkar ◽  
Ashutosh V. Bedekar
Keyword(s):  
Molecular Recognition ◽  
Fluorescence Spectroscopy ◽  
Simple Chemical ◽  
Chiral Solvating Agent ◽  
Optically Pure

Optically pure 2-(quinolin-8-yloxy)cyclohexan-1-ol 1, obtained via simple chemical and bio-catalytic steps, was used as a chiral solvating agent for molecular recognition of the enantiomers of acids.

ChemInform Abstract: Synthesis of Novel Acridino- and Phenazino-18-crown-6 Ligands and Their Optically Pure Dimethyl-Substituted Analogues for Molecular Recognition Studies.

ChemInform ◽  
2010 ◽  
Vol 30 (24) ◽  
pp. no-no
Author(s):  
Peter Huszthy ◽  
Erika Samu ◽  
Borbala Vermes ◽  
Gabriella Mezey-Vandor ◽  
Mihaly Nogradi ◽  
...  
Keyword(s):  
Molecular Recognition ◽  
Optically Pure

scholarly journals Molecular Recognition of the HPLC Whelk-O1 Selector towards the Conformational Enantiomers of Nevirapine and Oxcarbazepine

2020 ◽  
Vol 22 (1) ◽  
pp. 144
Author(s):  
Roberta Franzini ◽  
Marco Pierini ◽  
Andrea Mazzanti ◽  
Antonia Iazzetti ◽  
Alessia Ciogli ◽  
...  
Keyword(s):  
Molecular Recognition ◽  
Chiral Stationary Phase ◽  
Stationary Phases ◽  
Chiral Hplc ◽  
Chromatographic Separations ◽  
Recognition Mechanism ◽  
Ambient Temperatures ◽  
Fast Exchange ◽  
Optically Pure ◽  
Vt Nmr

The presence of stereogenic elements is a common feature in pharmaceutical compounds, and affording optically pure stereoisomers is a frequent issue in drug design. In this context, the study of the chiral molecular recognition mechanism fundamentally supports the understanding and optimization of chromatographic separations with chiral stationary phases. We investigated, with molecular docking, the interactions between the chiral HPLC selector Whelk-O1 and the stereoisomers of two bioactive compounds, the antiviral Nevirapine and the anticonvulsant Oxcarbazepine, both characterized by two stereolabile conformational enantiomers. The presence of fast-exchange enantiomers and the rate of the interconversion process were studied using low temperature enantioselective HPLC and VT-NMR with Whelk-O1 applied as chiral solvating agent. The values of the energetic barriers of interconversion indicate, for the single enantiomers of both compounds, half-lives sufficiently long enough to allow their separation only at critically sub-ambient temperatures. The chiral selector Whelk-O1 performed as a strongly selective discriminating agent both when applied as a chiral stationary phase (CSP) in HPLC and as CSA in NMR spectroscopy.

A Three-Dimensional Tetraphenylethylene-Based Fluorescence Covalent Organic Framework for Molecular Recognition

2020 ◽  
Author(s):  
Junxia Ren ◽  
Yaozu Liu ◽  
Xin Zhu ◽  
Yangyang Pan ◽  
Yujie Wang ◽  
...  
Keyword(s):  
Molecular Recognition ◽  
Fluorescence Probe ◽  
Three Dimensional ◽  
Hazardous Substances ◽  
Covalent Organic Framework ◽  
Highly Sensitive ◽  
Volatile Organic ◽  
Polycyclic Aromatic ◽  
Better Than ◽  
Organic Framework

<p><a></a><a></a><a></a><a></a><a></a><a></a><a></a><a>The development of highly-sensitive recognition of </a><a></a><a></a><a></a><a></a><a>hazardous </a>chemicals, such as volatile organic compounds (VOCs) and polycyclic aromatic hydrocarbons (PAHs), is of significant importance because of their widespread social concerns related to environment and human health. Here, we report a three-dimensional (3D) covalent organic framework (COF, termed JUC-555) bearing tetraphenylethylene (TPE) side chains as an aggregation-induced emission (AIE) fluorescence probe for sensitive molecular recognition.<a></a><a> </a>Due to the rotational restriction of TPE rotors in highly interpenetrated framework after inclusion of dimethylformamide (DMF), JUC-555 shows impressive AIE-based strong fluorescence. Meanwhile, owing to the large pore size (11.4 Å) and suitable intermolecular distance of aligned TPE (7.2 Å) in JUC-555, the obtained material demonstrates an excellent performance in the molecular recognition of hazardous chemicals, e.g., nitroaromatic explosives, PAHs, and even thiophene compounds, via a fluorescent quenching mechanism. The quenching constant (<i>K</i><sub>SV</sub>) is two orders of magnitude better than those of other fluorescence-based porous materials reported to date. This research thus opens 3D functionalized COFs as a promising identification tool for environmentally hazardous substances.</p>

Biomimetic Extracellular Vesicles Embedded with Black Phosphorus for Molecular Recognition-Guided Biomineralization

2018 ◽  
Author(s):  
Yingqian Wang ◽  
Xiaoxia Hu ◽  
Lingling Zhang ◽  
Chunli Zhu ◽  
Jie Wang ◽  
...  
Keyword(s):  
Molecular Recognition ◽  
Extracellular Vesicles ◽  
Inorganic Phosphate ◽  
Physiological Activity ◽  
Medical Engineering ◽  
Matrix Vesicles ◽  
Black Phosphorus ◽  
Photothermal Effect ◽  
Biological Processes ◽  
Extracellular Environment

Extracellular vesicles (EVs) are involved in the regulation of cell physiological activity and the reconstruction of extracellular environment. Matrix vesicles (MVs) are a type of EVs, and they participate in the regulation of cell mineralization. Herein, bioinspired MVs embedded with black phosphorus are functionalized with cell-specific aptamer (denoted as Apt-bioinspired MVs) for stimulating biomineralization. The aptamer can direct bioinspired MVs to targeted cells, and the increasing concentration of inorganic phosphate originated from the black phosphorus can facilitate cell biomineralization. The photothermal effect of the Apt-bioinspired MVs also positively affects mineralization. In addition, the Apt-bioinspired MVs display outstanding bone regeneration performance. Considering the excellent behavior of the Apt-bioinspired MVs for promoting biomineralization, our strategy provides a way of designing bionic tools for studying the mechanisms of biological processes and advancing the development of medical engineering.<br>

Arylboronic Acids in Self-condensation of Glucosamines Forming Deoxyfructosazine, Catalysts or Reagents?

2019 ◽  
Author(s):  
Meifeng Wang ◽  
Gan Zhu ◽  
Yiqun Li ◽  
Liuqun Gu
Keyword(s):  
Molecular Recognition ◽  
Boric Acid ◽  
Boronic Acid ◽  
Catalytic Mechanism ◽  
Organic Transformations ◽  
Food Industries ◽  
Arylboronic Acids ◽  
Excess Amount ◽  
Phenyl Boronic Acid ◽  
Boron Acid

Arylboronic acids were widely used as efficient catalysts in direct amide formation and other organic transformations. Surprisingly, reports on their use as catalysts in carbohydrates synthesis are very rare even though boron acid-diol complexation was extensively investigated in molecular recognition for saccharides and so on. Here we developed an efficient arylboronic acids catalyzed dimerization of glucosamines forming deoxyfructosazine which is important compound in pharmaceutical and food industries, against a commonly held belief that excess amount of phenyl boronic acid (or boric acid) is a must. A catalytic mechanism was also proposed and arylboronic acids instead of their boronates was identified as catalysts.

A Peptoid with Extended Shape in Water

2019 ◽  
Author(s):  
Jumpei Morimoto ◽  
Yasuhiro Fukuda ◽  
Takumu Watanabe ◽  
Daisuke Kuroda ◽  
Kouhei Tsumoto ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
Dimensional Space ◽  
Three Dimensional ◽  
Biomolecular Recognition ◽  
Biological Application ◽  
New Class ◽  
Proteolytic Resistance ◽  
Pharmacokinetic Properties ◽  
Optically Pure ◽  
Three Dimensional Space

<div> <div> <div> <p>“Peptoids” was proposed, over decades ago, as a term describing analogs of peptides that exhibit better physicochemical and pharmacokinetic properties than peptides. Oligo-(N-substituted glycines) (oligo-NSG) was previously proposed as a peptoid due to its high proteolytic resistance and membrane permeability. However, oligo-NSG is conformationally flexible and is difficult to achieve a defined shape in water. This conformational flexibility is severely limiting biological application of oligo-NSG. Here, we propose oligo-(N-substituted alanines) (oligo-NSA) as a new peptoid that forms a defined shape in water. A synthetic method established in this study enabled the first isolation and conformational study of optically pure oligo-NSA. Computational simulations, crystallographic studies and spectroscopic analysis demonstrated the well-defined extended shape of oligo-NSA realized by backbone steric effects. The new class of peptoid achieves the constrained conformation without any assistance of N-substituents and serves as an ideal scaffold for displaying functional groups in well-defined three-dimensional space, which leads to effective biomolecular recognition. </p> </div> </div> </div>

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