Neutral anion receptors: design and application

Antonisse, Martijn M. G.; Reinhoudt, David N.

doi:10.1039/a707529d

Cited by 348 publications

(179 citation statements)

References 61 publications

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“…2). Also the two-dimensional nuclear Overhauser effect NMR spectra of the two peptides in d 6 -DMSO are comparable. The most informative feature in both spectra is the crosspeak between the NH and the H(␣) signals, which demonstrates the close spatial proximity of the corresponding protons in both compounds.…”

Section: Resultsmentioning

confidence: 72%

“…Similarly to peptides 1 and 2, a crosspeak between the NH and H(␣) signals of the major conformer of 3 is visible in the nuclear Overhauser effect two-dimensional NMR spectrum in d 6 -DMSO. There is none, however, between the same signals of the minor conformer.…”

Section: Resultsmentioning

confidence: 99%

“…2), and also the NMR spectrum indicates a different conformational behavior of 3. Whereas 1 and 2 possess simple 1 H NMR spectra consistent with an averaged C 3 symmetrical conformation, in the spectrum of 3 in d 6 -DMSO at room temperature, two sets of signals in a ratio of ca. 1:10 are visible, each of which represents a C 3 -symmetrical peptide conformation (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…A way of mimicking these interactions in an artificial system is to arrange amide or urea NH groups around the cavity of a suitable host molecule. This strategy has led to the development of many artificial hosts for anions, some of which possess remarkable substrate affinity, even in highly competitive solvents such as DMSO or acetonitrile (4)(5)(6)(7)(8)(9)(10)(11)(12). The ultimate goal has, of course, been the design of receptors that bind anions by hydrogen bonds in water.…”

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confidence: 99%

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Conformation and anion binding properties of cyclic hexapeptides containing l -4-hydroxyproline and 6-aminopicolinic acid subunits

Kubik

Goddard

2002

Proc. Natl. Acad. Sci. U.S.A.

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Two cyclic hexapeptides containing alternating all R and all S configured L-(4R͞S)-hydroxyproline and 6-aminopicolinic acid subunits are presented, and the influence of the hydroxyl groups on the solubility, conformation, and receptor properties is investigated. Cyclopeptide 2, containing the natural 4R configured hydroxyproline, adopts a conformation similar to that of the unsubstituted peptide 1, which is able to bind anions such as halides and sulfate in aqueous solution. 2 also interacts with these anions, but whereas 1 forms sandwich type 2:1 complexes, in which the anion is bound by two cyclopeptide moieties, 2 forms 1:1 complexes. The stabilities of the halide and sulfate complexes of 2 range between 10 0 and 10 2 M ؊1 in 80% D2O͞CD3OD. Complex formation is detectable even in water, but with slightly smaller stability constants. Using this information a quantitative evaluation of the stability of the 2:1 complexes of 1, for which overall stability constants in the order 10 4 to 10 5 M ؊2 in 80% D2O͞CD3OD were observed, was made. In contrast to 2, the conformation of 3, containing the non-natural 4S configured hydroxyproline, is strongly affected by the presence of the hydroxyl groups. In d 6-DMSO and methanol͞water mixtures a slow conformational equilibrium between two C3-symmetrical conformers is observed, and 3 is thus much less preorganized for anion binding than either 1 or 2.T he crystal structures of anion binding proteins with the substrate resting in the active site have provided valuable information on the principles nature uses for the recognition of negatively charged compounds (1). Important binding interactions are, for example, multiple hydrogen bonds formed between the substrate and NH groups of the protein backbone or hydrogen bond donors in amino acid side chains (2, 3). A way of mimicking these interactions in an artificial system is to arrange amide or urea NH groups around the cavity of a suitable host molecule. This strategy has led to the development of many artificial hosts for anions, some of which possess remarkable substrate affinity, even in highly competitive solvents such as DMSO or acetonitrile (4-12). The ultimate goal has, of course, been the design of receptors that bind anions by hydrogen bonds in water. However, despite the recent advances in the development of anion receptors (4-7), most systems described so far require strong electrostatic or coordinative interactions to be effective in this solvent. One of the few exceptions is the cyclic hexapeptide 1 that has recently been described by us (13). This neutral macrocyclic receptor interacts with anions such as halides or sulfate even in water͞methanol mixtures, a behavior that can largely be attributed to the special geometry of the complexes formed. We have found that the presence of a suitable anion in solution induces an aggregation of two cyclopeptide molecules, whereby a cavity is formed into which the anion is included (Fig. 1). In this complex, the anion is shielded from the surrounding solvent and can thus inte...

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Section: Resultsmentioning

confidence: 72%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

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Conformation and anion binding properties of cyclic hexapeptides containing l -4-hydroxyproline and 6-aminopicolinic acid subunits

Kubik

Goddard

2002

Proc. Natl. Acad. Sci. U.S.A.

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“…Anion supramolecular chemistry involves the development and use of selective anion receptors. [1][2][3][4][5][6][7][8][9][10][11][12][13][14] In fact, today a large number of coordination studies can be found in the literature describing a wide range of different ligands for anion coordination mainly involving hydrogen bonding, [15][16][17][18][19] electrostatic interactions [20][21][22][23][24][25][26][27] or coordination with suitable metal cations. [28][29][30][31][32][33] The nature of the binding sites and their specific spatial arrangement determine the binding constant with a certain anion and usually selective coordination can be found when a large host-guest complementarity is reached.…”

Section: -Introductionmentioning

confidence: 99%

Chromogenic and fluorogenic chemosensors and reagents for anions. A comprehensive review of the year 2009

2011

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New Boronic-Acid- and Boronate-Substituted Aromatic Compounds as Precursors of Fluoride-Responsive Conjugated Polymer Films

et al. 2000

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New electropolymerizable aromatic compounds (i.e. pyrrole, thiophene, aniline) bearing boronic acid and ester substituents have been synthesized and their electrochemical behavior has been investigated. Functionalized polythiophene and polypyrrole films could be anodically generated in acetonitrile, whereas the polyaniline derivative was electroformed in an acidic aqueous solution. The electrochemical responses of some of these materials were changed when fluoride ions were added to the electrolytic solutions. The strongest modifications, caused by binding of fluoride by the immobilized boron, were observed for the polypyrrole derivative in hydroorganic media.

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Neutral anion receptors: design and application

Cited by 348 publications

References 61 publications

Conformation and anion binding properties of cyclic hexapeptides containing l -4-hydroxyproline and 6-aminopicolinic acid subunits

Conformation and anion binding properties of cyclic hexapeptides containing l -4-hydroxyproline and 6-aminopicolinic acid subunits

Chromogenic and fluorogenic chemosensors and reagents for anions. A comprehensive review of the year 2009

New Boronic-Acid- and Boronate-Substituted Aromatic Compounds as Precursors of Fluoride-Responsive Conjugated Polymer Films

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