2001
DOI: 10.1002/1521-3773(20010716)40:14<2648::aid-anie2648>3.0.co;2-#
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Abstract: A neutral receptor that binds anions by hydrogen bonds even in water is the cyclopeptide reported in this article. This property results from the particular structure of the complex in which the anions are effectively shielded from the surrounding solvent, as can be seen in the iodide complex shown.

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Cited by 132 publications
(71 citation statements)
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“…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.…”
supporting
confidence: 86%
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“…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.…”
supporting
confidence: 86%
“…The NH signal is shifted because of hydrogen bond formation between the anions and the amide protons. This interaction brings the anions into close proximity to the H(␣) protons, so that their resonance is also affected (13). In protic solvents, in which the NH protons are in fast exchange with the solvent protons, the shift of the H(␣) signal is still clearly detectable, thus allowing investigations on anion binding even in these solvents.…”
Section: Resultssupporting
confidence: 58%
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“…45,46 Conversely, replacing the Aba residues in receptor 16 with 6-aminopicolinic acid (Apa) residues yields cyclic hexapeptides such as 18 in which the ring nitrogens of the aromatic subunits induce a converging arrangement of the NH binding sites, resulting in an increase in anion affinity. 47 1 H NMR experiments indicated that while the affinity of 16 for iodide in DMSO is extremely low, the association constant of the iodide complex of 18 amounts to 150 M À1 in the same solvent. 27 Interestingly, 18 was shown to associate with anions in highly competitive protic solvent mixtures such as 80% D 2 O-CD 3 OD where 2 : 1 sandwich-type complexes with Cl À , Br À , I À and SO 4 2À were formed as evidenced by Job's plot, mass spectrometric and X-ray crystal structure analysis (Fig.…”
Section: Backbone Modified Cyclic Peptidesmentioning
confidence: 99%