Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition

Zhao, Cunyuan; Yao, Huan; Li, Shi-Yao; Du, Fang; Wang, Lili; Yang, Liu‐Pan

doi:10.1016/j.cclet.2023.108879

Chinese Chemical Letters

2024

DOI: 10.1016/j.cclet.2023.108879

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Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition

Cunyuan Zhao

Huan Yao

Shi-Yao Li

et al.

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Cited by 8 publications

References 70 publications

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Precise Recognition in Water by an Endo‐Functionalized Cavity: Tuning the Complementarity of Binding Sites

Wang,

Zhang

et al. 2023

Angewandte Chemie

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Precise binding towards structurally similar substrates is a common feature of biomolecular recognition. However, achieving such selectivity—especially in distinguishing subtle differences in substrates—with synthetic hosts can be quite challenging. Herein, we report a novel design strategy involving the combination of different rigid skeletons to adjust the distance between recognition sites within the cavity, which allows for the highly selective recognition of hydrogen‐bonding complementary substrates, such as 4‐chromanone. X‐ray single‐crystal structures and density functional theory calculations confirmed that the distance of endo‐functionalized groups within the rigid cavity is crucial for achieving high binding selectivity through hydrogen bonding. The thermodynamic data and molecular dynamics simulations revealed a significant influence of the hydrophobic cavity on the binding affinity. The new receptor possesses both high selectivity and high affinity, which provide valuable insights for the design of customized receptors.

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Precise Recognition in Water by an Endo‐Functionalized Cavity: Tuning the Complementarity of Binding Sites

Wang,

Zhang

et al. 2023

Angewandte Chemie

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Precise Recognition in Water by an Endo‐Functionalized Cavity: Tuning the Complementarity of Binding Sites

Wang,

Zhang

et al. 2023

Angew Chem Int Ed

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Ether Naphthotube Host‐Guest Complexes and [2]Rotaxanes with Dications

Zheng,

Wang,

Jiang

et al. 2024

Chemistry A European J

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The interactions between ether naphthotube and a series of dication guests in organic solution were investigated. It was found that ether naphthotube formed stable host‐guest complexes selectively with these guests in a 1:1 stoichiometric ratio with association constants ranging from 102 to 106 M‐1, which were confirmed by 1H‐NMR spectra and ITC experiments. The host‐guest interactions are driven by enthalpy change as the entropic factors are unfavorable. Positive correlations between ΔH and ΔS have been observed in the host‐guest complexes. Furthermore, the para‐substitution of the guests can significantly affect the binding affinities through a combination of field/inductive and resonance effects by following a linear free energy relationship. Based on the host‐guest complexes composed of ether naphthotube and organic cations, two interlocked [2]rotaxanes were prepared by cationization reaction and Huisgen cycloaddition between the cations and the stopper components. The ether naphthotube‐based host‐guest complexes are useful for creating sophisticated interlocked molecules.

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Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition

Cited by 8 publications

References 70 publications

Precise Recognition in Water by an Endo‐Functionalized Cavity: Tuning the Complementarity of Binding Sites

Precise Recognition in Water by an Endo‐Functionalized Cavity: Tuning the Complementarity of Binding Sites

Precise Recognition in Water by an Endo‐Functionalized Cavity: Tuning the Complementarity of Binding Sites

Ether Naphthotube Host‐Guest Complexes and [2]Rotaxanes with Dications

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