Anion Recognition by Neutral Macrocyclic Azole Amides

Schnopp, Markus; Ernst, Silvia; Haberhauer, Gebhard

doi:10.1002/ejoc.200800811

Cited by 30 publications

(31 citation statements)

References 49 publications

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“…519 Proton NMR spectroscopy supported the presence of hydrogen bonding between the amide NH group and azole nitrogen atom, which was expected to preorganize the binding cavity in the conformation shown. The anion binding ability of these macrocycles was evaluated by means of 1 H NMR spectroscopic titrations carried out in DMSO- d 6 / 5% CDCl 3 using the TBA anion salts.…”

Section: Major Phosphate-binding Functionalitiesmentioning

confidence: 92%

Artificial Receptors for the Recognition of Phosphorylated Molecules

et al. 2011

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Section: Major Phosphate-binding Functionalitiesmentioning

confidence: 92%

Artificial Receptors for the Recognition of Phosphorylated Molecules

et al. 2011

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“…The distance between the nitrogen atoms N14 and N14' in a derivative of 13 amounts to 11.19 , whereas the same distance in a derivative of 12 is only 6.85 . [13] Bridge 8 shows a better tension angle because the aromatic substituents are arranged at an angle of 1208. Accordingly, the connection of 8 with both clamps was performed without any difficulties.…”

Section: Synthesismentioning

confidence: 98%

A Unidirectional Open–Close Mechanism of Metal‐Ion‐Driven Molecular Hinges with Adjustable Amplitude

Ernst

Haberhauer

2009

Chemistry A European J

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A basic requirement for each molecular system that is supposed to perform work is a synchronized and unidirectional movement. Unidirectionality can be achieved by a change of configuration or conformation that is controllable by external stimulation. Molecular hinges based on a bipyridine unit work unidirectionally and are able to reach an amplitude of motion that amounts to about 180 degrees. To analyze if it is possible to adjust the height of the unidirectional amplitude of motion, three planar chiral molecular hinge systems with a 2,2'-bipyridine unit as functional element were designed and stimulated with various divalent metal ions in different solvents. The configurations of the hinges were determined by DFT calculations using B3LYP and the 6-31G* basis set and experimentally verified by 2D NMR NOESY spectra. Circular dichroism (CD) and UV spectroscopy were used to study the properties of the hinges by the addition of metal ions (primarily Zn(2+) and Hg(2+)) in dichloromethane and methanol. The choice of metal ions and solvents determines whether or not and how far the hinges are closed. Furthermore, a drastic change in the height of the amplitude of motion can be reached by modifying the position of the bipyridine unit in the hinge. Amplitude values from 45 up to 190 degrees were obtained from quantum mechanical calculations. This control of the amplitude of motion can in the future be used for more complex switching processes of molecular machines.

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“…[68][69][70][71] The series of C 2 -symmetric azole-containing macrocyclic peptides 41-44 were reported in 2009 and their ability to bind anions was studied in detail. 72 …”

Section: View Article Onlinementioning

confidence: 99%

Anion recognition by cyclic peptides

Elmes

Jolliffe

2015

Chem. Commun.

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Anion binding selectivity can often be controlled by judicious arrangement of recognition moieties around an anion of interest. Indeed, nature takes advantage of large peptides/proteins to provide highly efficient and selective anion receptors using a small number of amino acid building blocks placed in a precise arrangement. Cyclic peptides are ideal synthetic scaffolds to position binding residues in a similarly preorganised manner as their synthetic versatility and rigidified structure allows precise control over their size and shape. This review summarises the recent use of such cyclic peptide scaffolds as receptors for various anionic species.

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Anion Recognition by Neutral Macrocyclic Azole Amides

Cited by 30 publications

References 49 publications

Artificial Receptors for the Recognition of Phosphorylated Molecules

Artificial Receptors for the Recognition of Phosphorylated Molecules

A Unidirectional Open–Close Mechanism of Metal‐Ion‐Driven Molecular Hinges with Adjustable Amplitude

Anion recognition by cyclic peptides

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