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
Hauptverfasser: Zuo, Wei, Jia, Chuandong, Zhang, Huizheng, Zhao, Yanxia, Yang, Xiao-Juan, Wu, Biao
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Sprache:eng
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Zusammenfassung: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.
ISSN:2041-6520
2041-6539
DOI:10.1039/C8SC04338H