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Selective recognition of choline phosphate by tripodal hexa-urea receptors with dual binding sites: crystal and solution evidence.

ABSTRACT: 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 Me3N-+ 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.

SUBMITTER: Zuo W

PROVIDER: S-EPMC6385852 | biostudies-other | 2019 Feb

REPOSITORIES: biostudies-other

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Selective recognition of choline phosphate by tripodal hexa-urea receptors with dual binding sites: crystal and solution evidence.

Zuo Wei W Jia Chuandong C Zhang Huizheng H Zhao Yanxia Y Yang Xiao-Juan XJ Wu Biao B

Chemical science 20181227 8

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 envi ...[more]

PMID: 30881678

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