Selective recognition of choline phosphate by tripodal hexa-urea receptors with dual binding sites: crystal and solution evidence
Two tripodal hexa-urea receptors functionalized with aromatic terminal groups are capable of binding choline phosphate (CP). Crystal structures of the host-guest complexes reveal that the zwitterion CP is efficiently encapsulated in the tripodal hosts in a dual-site binding mode. The phosphate tail...
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| Veröffentlicht in: | Chemical science (Cambridge) 2019-02, Vol.10 (8), p.2483-2488 |
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| creator | Zuo, Wei Jia, Chuandong Zhang, Huizheng Zhao, Yanxia Yang, Xiao-Juan Wu, Biao |
| description | Two tripodal hexa-urea receptors functionalized with aromatic terminal groups are capable of binding choline phosphate (CP). Crystal structures of the host-guest complexes reveal that the zwitterion CP is efficiently encapsulated in the tripodal hosts in a dual-site binding mode. The phosphate tail of CP is coordinated by the urea groups and the quaternary ammonium head is bound in a 'composite aromatic box' through cation-π and hydrogen-bonding interactions. Such a partial aromatic binding environment for the Me
N-
cation mimics that of most enzymes catalyzing the conversion of quaternary ammonium substrates. Moreover, NMR, ESI-MS, and fluorescence studies demonstrate the selective binding and sensing of CP over other competing species such as ADP, ATP, choline and derivatives. |
| doi_str_mv | 10.1039/C8SC04338H |
| format | Article |
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N-
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N-
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N-
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| source | DOAJ Directory of Open Access Journals; PubMed Central Open Access; EZB-FREE-00999 freely available EZB journals; PubMed Central |
| subjects | Binding sites Cations Choline Crystal structure Crystallography Fluorescence Hydrogen bonding NMR Nuclear magnetic resonance Receptors Selective binding Substrates Ureas Zwitterions |
| title | Selective recognition of choline phosphate by tripodal hexa-urea receptors with dual binding sites: crystal and solution evidence |
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