Binding of acetylcholine and quaternary ammonium compounds to a C3-symmetric bowl-shaped tripeptide of 2-(3-aminophenoxy)propanoic acids acting as a ditopic receptor

Akazome, Motohiro; Hamada, Norihiro; Takagi, Koji; Yagyu, Daisuke; Matsumoto, Shoji

doi:10.1016/j.tetlet.2014.02.066

Cited by 5 publications

(9 citation statements)

References 39 publications

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“…This system is characterized by a bowl-like structure with C 3 -symmetry and acts as a receptor for both acetylcholine chloride (AChCl) and benzylmethylammonium salts (Figure 9a). 44 The cavity size and restricted conformation allow the ammonium cation to be accommodated via cation−π interactions. 1 H NMR spectroscopic analyses led to the conclusion that, in CDCl 3 solution, receptor 11 forms a 1:1 complex with AChCl with the ammonium cation bound into the cavity via cation−π interactions.…”

Section: Organic Cations and Inorganic Anions As Ion Pairsmentioning

confidence: 99%

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: Organic Cations and Inorganic Anions As Ion Pairsmentioning

confidence: 99%

Macrocycles as Ion Pair Receptors

et al. 2019

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“…[20] In a biomimetic approach, Akazome and co-workers reported a novel tripeptide bowl-like receptor, 7 (Figure 6a), for the neurotransmitter acetylcholine chloride (ACh • Cl). [21] Preliminary 1 H NMR titration experiments in CDCl 3 revealed 7 was capable of binding ACh • Cl with strong affinity K a = 1640 M À 1 ; in contrast, TBACl was bound much less strongly K a = 252 M À 1 . Further studies including X-ray crystallography, 1 H-1 H NOE NMR spectroscopy, and MD simulations demonstrated that Cl À complexation by 7 was accompanied by a flipping of amide HB donors to convergently bind the halide.…”

Section: Binding Motifsmentioning

confidence: 96%

From Heteroditopic to Multitopic Receptors for Ion‐Pair Recognition: Advances in Receptor Design and Applications

2020

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Ion‐pair recognition has emerged from cation and anion recognition and become a diverse and active field in its own right. The last decade has seen significant advances in receptor design in terms of the types of binding motifs, understanding of cooperativity and increase in complexity from heteroditopic to multitopic receptors. As a result, attention has turned to applying this knowledge to the rational design of ion‐pair receptors for applications in salt solubilisation and extraction, membrane transport and sensing. This Review highlights recent progress and developments in the design and applications of heteroditopic and multitopic receptors for ion‐pair recognition.

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“…[α] D +64 ( c 1, CHCl 3 ), (ref. [α] D +64.4 ( c 0.10, CHCl 3 ) [ 29 ]). 1 H-NMR (270 MHz, CDCl 3 ): δ = 8.18 (d, J = 8.6 Hz, 2H), 6.93 (d, J = 9.2 Hz, 2H), 4.90 (q, J = 6.8 Hz, 1H), 3.78 (s, 3H), 1.68 d, J = 6.8 Hz, 3H).…”

Section: Methodsmentioning

confidence: 99%

“…An example of the synthesis of racemic azide-based lactisole ethyl ester has been reported previously [26], but to date, the asymmetric synthesis of azide modified on the aromatic ring of the lactisole skeleton has not been reported. Akazome et al reported the asymmetric synthesis of (R)-2-nitro (R)-23 [27] and (R)-3-nitro (R)-15 [28,29]-substituted lactisole methyl ester. Our retrosynthesis for comprehensive preparations of azide-based lactisole derivatives was based on the asymmetric synthesis of nitro-substituted lactisole skeletons, followed by the conversion of the nitro group to azide derivatives.…”

Section: Azide-based Lactisole Derivativesmentioning

confidence: 99%

Asymmetric Synthesis of Photophore-Containing Lactisole Derivatives to Elucidate Sweet Taste Receptors

et al. 2020

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Lactisole, which has a 2-phenoxy propionic acid skeleton, is well-known as an inhibitor of sweet taste receptors. We recently revealed some of the structure–activity relationships of the aromatic ring and chiral center of lactisole. Photoaffinity labeling is one of the common chemical biology methods to elucidate the interaction between bioactive compounds and biomolecules. In this paper, the novel asymmetric synthesis of lactisole derivatives with common photophores (benzophenone, azide and trifluoromethyldiazirine) for photoaffinity labeling is described. The synthetic compounds are subjected to cell-based sweet taste receptors, and the substitution with trifluoromethyldiazirinyl photophore shows the highest affinity to the receptor of the synthesized compounds.

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Binding of acetylcholine and quaternary ammonium compounds to a C3-symmetric bowl-shaped tripeptide of 2-(3-aminophenoxy)propanoic acids acting as a ditopic receptor

Cited by 5 publications

References 39 publications

Macrocycles as Ion Pair Receptors

Macrocycles as Ion Pair Receptors

From Heteroditopic to Multitopic Receptors for Ion‐Pair Recognition: Advances in Receptor Design and Applications

Asymmetric Synthesis of Photophore-Containing Lactisole Derivatives to Elucidate Sweet Taste Receptors

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