Selective recognition of methyl viologen by an endo-functionalized naphthobox

Liu, Weier; Kong, Linghui; Quan, Mao; Yao, Huan; Yang, Liu‐Pan; Au‐Yeung, Ho Yu; Jiang, Wei

doi:10.1016/j.cclet.2022.02.076

“…To our knowledge, there has not been any research on distinguishing structurally similar guests in water via customized artificial receptors. For precise recognition of structurally similar substrates, directional noncovalent interactions should be combined with a rigid cavity [16] . Furthermore, the structure of the rigid skeleton should be replaceable to enable the complementarity between the polar binding sites of the receptor and substrates (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

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

Wang,

Zhang

et al. 2023

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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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“…This high selectivity was consistent with the selective recognition of methyl viologen by an endo -functionalized naphthobox. 36…”

Section: Resultsmentioning

confidence: 99%

“…This high selectivity was consistent with the selective recognition of methyl viologen by an endo-functionalized naphthobox. 36 Formation of ternary assemblies through the collaboration of 1 4+ and SC4 4− Bearing in mind that 1•(PF 6 ) 4 and SC4H can form a stable boxin-box supramolecular assembly in both the solid state and solution, and there is a void inside SC4H that is large enough to potentially accommodate a second guest, we thus sought out guest molecules that could occupy this cavity. The high affinity cytosine (CTS) and the low affinity antifungal drug 5-fluorocytosine (5F-CTS) discovered from ITC screening were employed as the guests in order to investigate the possibility of forming ternary assemblies.…”

Section: Recognition Of Natural Epigenetically and Chemically Modifie...mentioning

confidence: 99%

A box-in-box supramolecular assembly for the highly selective recognition of natural, epigenetically and chemically modified cytosines in water

Qin,

Xu,

Wang

et al. 2024

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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.

show abstract

Selective recognition of methyl viologen by an endo-functionalized naphthobox

Cited by 6 publications

References 44 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

A box-in-box supramolecular assembly for the highly selective recognition of natural, epigenetically and chemically modified cytosines in water

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

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