Crystal Structures of Resorcin[4]arene and Tetramethylated Resorcin[4]arene Complexes Incorporating <scp>l</scp>-Carnitine through Cation–π Interaction

Fujisawa, Ikuhide; Takeuchi, Daiki; Kato, Ryo; Murayama, Kazutaka; Aoki, Katsuyuki

doi:10.1246/bcsj.20110166

Cited by 9 publications

(3 citation statements)

References 44 publications

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“…They were then tested for their ability to recognize specific biological substrates, such as carnitine. While the unnatural antipode, d -carnitine, is devoid of a recognized biological role, the naturally occurring l -carnitine is involved in fatty acid transport through the formation of fatty acid-carnitine esters. − PL -181 was found to bind l -carnitine with an association constant of (4.1 ± 0.3) × 10 3 M –1 and a 1:1 stoichiometry, as inferred from 1 H NMR spectroscopic analyses carried out in CD 3 CN. Molecular modeling studies led to the suggestion that receptor PL -181 binds l -carnitine in a ditopic fashion with the carnitine carboxylate group stabilized by the cyclic peptide moiety via hydrogen-bonding interactions.…”

Section: Recognition With Macrocyclic Ion Pair Receptorsmentioning

confidence: 91%

Macrocycles as Ion Pair Receptors

et al. 2019

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Cation and anion recognition have both played central roles in the development of supramolecular chemistry. Much of the associated research has focused on the development of receptors for individual cations or anions, as well as their applications in different areas. Rarely is complexation of the counterions considered. In contrast, ion pair recognition chemistry, emerging from cation and anion coordination chemistry, is a specific research field where co-complexation of both anions and cations, so-called ion pairs, is the center of focus. Systems used for the purpose, known as ion pair receptors, are typically di-or polytopic hosts that contain recognition sites for both cations and anions and which permit the concurrent binding of multiple ions. The field of ion pair recognition has blossomed during the past decades. Several smaller reviews on the topic were published roughly 5 years ago. They provided a summary of synthetic progress and detailed the various limiting ion recognition modes displayed by both acyclic and macrocyclic ion pair receptors known at the time. The present review is designed to provide a comprehensive and up-to-date overview of the chemistry of macrocycle-based ion pair receptors. We specifically focus on the relationship between structure and ion pair recognition, as well as applications of ion pair receptors in sensor development, cation and anion extraction, ion transport, and logic gate construction. CONTENTS 3.4.

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Section: Recognition With Macrocyclic Ion Pair Receptorsmentioning

confidence: 91%

Macrocycles as Ion Pair Receptors

et al. 2019

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“…25,26 The ammonium group is particularly important in biotechnology since it constitutes part of many active pharmaceutical compounds. [27][28][29] A recent trend is the co-crystallization of some pharmaceutical compounds with receptors like resorcinarenes and pyrogallarenes with the hope of improving their pharmaceutical properties, 30,31 making crystal engineering 32 a useful tool in analysing supramolecular assemblies. A recent example is the co-crystallization of the pharmaceutical drug gabapentin, a primary amine widely used for the treatment of epilepsy and neuropathic pain, 33,34 with pyrogallarenes, which was studied by Atwood et al 30 Secondary and tertiary ammonium salts possess the hydrogen bond donating groups -NH 2 and -NH, respectively, and these can further enhance their complexation through intermolecular hydrogen bonds.…”

Section: Introductionmentioning

confidence: 99%

Encapsulation of secondary and tertiary ammonium salts by resorcinarenes and pyrogallarenes: the effect of size and charge concentration

2015

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The binding of different categories of alkyl ammonium (secondary and tertiary mono-and diammonium) salts by resorcinarenes and a pyrogallarene through weak interactions were analysed in all phases. 1 H NMR spectroscopy and electrospray ionisation mass spectrometry were utilized in analysing the complexes in solution and in the gas phase respectively. The 1 H NMR titration studies in methanol-d 4 reveal the association constants for the 1:1 complexes to vary according to the electronic properties of hosts as well as the size, geometric orientation and charge concentration of the guest cations with binding constants of up to 950 M -1 in some cases. Mass spectrometry reveals 1:1 monomeric and 1:2 dimeric complexes in the gas phase. Six co-crystals, three of which are dimeric host-guest capsular assemblies, two open inclusion complexes and a pseudocapsular methanol solvate were analysed in the solid state through single-crystal X-ray diffraction. The crystal structures confirm the complexes to be held together by multiple cation···π, CH···π and hydrogen bond interactions.

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“…In many kinds of protein architectures recognizing molecules with trimethylammonium groups, the cation−π interactions play important roles for recognition and binding [21,22]. In the Cambridge Structural Database (CSD), just one betaine structure among about one hundred fifteen reported betaine structures seems to form the cation−π interaction, though it is not clear whether the cation−π interaction is critical for the structure formation, because many other hydrogen bonds are formed simultaneously.…”

Section: Introductionmentioning

confidence: 99%

Glycine Betaine Recognition through Cation−π Interactions in Crystal Structures of Glycine Betaine Complexes with C-Ethyl-pyrogallol[4]arene and C-Ethyl-resorcin[4]arene as Receptors

Fujisawa

Aoki

2013

Crystals

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Abstract:The glycine betaine (betaine), interacts with several types of proteins with diverse structures in vivo, and in the contact regions, the aromatic rings of protein residues are frequently found beside the trimethylammonium group of betaine, implying the importance of the cation−π interactions in recognition of this molecule. The crystal structures determined by X-ray crystallography of the complexes of betaine and C-ethyl-pyrogallol[4]arene (pyrogallol cyclic tetramer: PCT) and betaine and C-ethyl-resorcin[4]arene (resorcinol cyclic tetramer: RCT) mimic the conformations of betaine and protein complexes and show that the clathrate conformations are retained by the cation−π interactions. The difference of the conformation feature of betaine in the Protein Data Bank and in the Cambridge Structural Database was found by chance during the research and analyzed with the torsion angles.

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Crystal Structures of Resorcin[4]arene and Tetramethylated Resorcin[4]arene Complexes Incorporating l-Carnitine through Cation–π Interaction

Cited by 9 publications

References 44 publications

Macrocycles as Ion Pair Receptors

Macrocycles as Ion Pair Receptors

Encapsulation of secondary and tertiary ammonium salts by resorcinarenes and pyrogallarenes: the effect of size and charge concentration

Glycine Betaine Recognition through Cation−π Interactions in Crystal Structures of Glycine Betaine Complexes with C-Ethyl-pyrogallol[4]arene and C-Ethyl-resorcin[4]arene as Receptors

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