Tetraphenylethene-based tetracationic cyclophanes and their selective recognition for amino acids and adenosine derivatives in water

2019 ◽  
Vol 55 (16) ◽  
pp. 2372-2375 ◽  
Author(s):  
Lin Cheng ◽  
Haiyang Zhang ◽  
Yunhong Dong ◽  
Yanxia Zhao ◽  
Yang Yu ◽  
...  
Keyword(s):  
Amino Acids ◽  
Selective Recognition ◽  
Π Interactions ◽  
Adenosine Derivatives

Tetracationic cyclophane 1 with a trapezoid-like cavity exhibited highly-selective recognition for tryptophan and ATP through electrostatic and π–π interactions in water.

scholarly journals Selective Recognition of Amino Acids and Peptides by Small Supramolecular Receptors

Molecules ◽  
2020 ◽  
Vol 26 (1) ◽  
pp. 106
Author(s):  
Joana N. Martins ◽  
João Carlos Lima ◽  
Nuno Basílio
Keyword(s):  
Amino Acids ◽  
Selective Recognition ◽  
Great Promise ◽  
Macrocyclic Compounds ◽  
Synthetic Receptors ◽  
Small Peptides ◽  
Molecular Imprinted Polymers ◽  
Polymeric Systems ◽  
Physiological Conditions ◽  
Level Information

To this day, the recognition and high affinity binding of biomolecules in water by synthetic receptors remains challenging, while the necessity for systems for their sensing, transport and modulation persists. This problematic is prevalent for the recognition of peptides, which not only have key roles in many biochemical pathways, as well as having pharmacological and biotechnological applications, but also frequently serve as models for the study of proteins. Taking inspiration in nature and on the interactions that occur between several receptors and peptide sequences, many researchers have developed and applied a variety of different synthetic receptors, as is the case of macrocyclic compounds, molecular imprinted polymers, organometallic cages, among others, to bind amino acids, small peptides and proteins. In this critical review, we present and discuss selected examples of synthetic receptors for amino acids and peptides, with a greater focus on supramolecular receptors, which show great promise for the selective recognition of these biomolecules in physiological conditions. We decided to focus preferentially on small synthetic receptors (leaving out of this review high molecular weight polymeric systems) for which more detailed and accurate molecular level information regarding the main structural and thermodynamic features of the receptor biomolecule assemblies is available.

On the interaction between the imidazolium cation and aromatic amino acids. A computational study

2015 ◽  
Vol 13 (29) ◽  
pp. 7961-7972 ◽  
Author(s):  
Ana A. Rodríguez-Sanz ◽  
Enrique M. Cabaleiro-Lago ◽  
Jesús Rodríguez-Otero
Keyword(s):  
Amino Acids ◽  
Computational Study ◽  
Aromatic Amino Acids ◽  
Imidazolium Cation ◽  
Π Interactions

Phe, Tyr and Trp form parallel complexes with cation⋯π interactions. His complexes are the strongest, but without making contact with the aromatic cloud.

Cadmium(ii) carboxyphosphonates based on mixed ligands: syntheses, crystal structures and recognition properties toward amino acids

RSC Advances ◽  
2016 ◽  
Vol 6 (95) ◽  
pp. 92175-92185 ◽  
Author(s):  
Zhou Zhao ◽  
Dan Yang ◽  
Bo Xing ◽  
Chao Ma ◽  
Zhen-Gang Sun ◽  
...  
Keyword(s):  
Amino Acids ◽  
Crystal Structures ◽  
Selective Recognition ◽  
Luminescence Properties ◽  
Mixed Ligands

Three novel cadmium(ii) carboxyphosphonates have been hydrothermally synthesized. The luminescence properties of compounds 1–3 have been investigated. Meanwhile, the excellent abilities of compounds 2 and 3 for selective recognition of tryptophan (Trp) have been demonstrated.

Serine and Cysteine π-Interactions in Nature: A Comparison of the Frequency, Structure, and Stability of Contacts Involving Oxygen and Sulfur

2015 ◽  
Vol 68 (3) ◽  
pp. 385 ◽  
Author(s):  
Hanzala B. Hussain ◽  
Katie A. Wilson ◽  
Stacey D. Wetmore
Keyword(s):  
Amino Acids ◽  
High Resolution ◽  
Protein Stability ◽  
Crystal Structures ◽  
Protein Complexes ◽  
Aromatic Amino Acids ◽  
Biological Macromolecules ◽  
Great Stability ◽  
Π Interactions ◽  
And Function

Despite many DNA–protein π-interactions in high-resolution crystal structures, only four X–H···π or X···π interactions were found between serine (Ser) or cysteine (Cys) and DNA nucleobase π-systems in over 100 DNA–protein complexes (where X = O for Ser and X = S for Cys). Nevertheless, 126 non-covalent contacts occur between Ser or Cys and the aromatic amino acids in many binding arrangements within proteins. Furthermore, Ser and Cys protein–protein π-interactions occur with similar frequencies and strengths. Most importantly, due to the great stability that can be provided to biological macromolecules (up to –20 kJ mol–1 for neutral π-systems or –40 kJ mol–1 for cationic π-systems), Ser and Cys π-interactions should be considered when analyzing protein stability and function.

scholarly journals Selective recognition of aromatic hydrocarbons by endo-functionalized molecular tubes via C/N-H⋅⋅⋅ π interactions

2018 ◽  
Vol 29 (1) ◽  
pp. 91-94 ◽  
Author(s):  
Guo-Bao Huang ◽  
Wei-Er Liu ◽  
Arto Valkonen ◽  
Huan Yao ◽  
Kari Rissanen ◽  
...  
Keyword(s):  
Aromatic Hydrocarbons ◽  
Selective Recognition ◽  
Π Interactions ◽  
Molecular Tubes

scholarly journals Cation-π Interactions Involving Aromatic Amino Acids

2007 ◽  
Vol 137 (6) ◽  
pp. 1504S-1508S ◽  
Author(s):  
Dennis A. Dougherty
Keyword(s):  
Amino Acids ◽  
Aromatic Amino Acids ◽  
Π Interactions

Probing Eudesmane Cation−π Interactions in Catalysis by Aristolochene Synthase with Non-canonical Amino Acids

2011 ◽  
Vol 133 (35) ◽  
pp. 13906-13909 ◽  
Author(s):  
Juan A. Faraldos ◽  
Alicja K. Antonczak ◽  
Verónica González ◽  
Rebecca Fullerton ◽  
Eric M. Tippmann ◽  
...  
Keyword(s):  
Amino Acids ◽  
Π Interactions ◽  
Aristolochene Synthase
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