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Title: Selective binding of choline by a phosphate-coordination-based triple helicate featuring an aromatic box

In nature, proteins have evolved sophisticated cavities tailored for capturing target guests selectively among competitors of similar size, shape, and charge. The fundamental principles guiding the molecular recognition, such as self-assembly and complementarity, have inspired the development of biomimetic receptors. In the current work, we report a self-assembled triple anion helicate (host 2) featuring a cavity resembling that of the choline-binding protein ChoX, as revealed by crystal and density functional theory (DFT)-optimized structures, which binds choline in a unique dual-site-binding mode. Here, this similarity in structure leads to a similarly high selectivity of host 2 for choline over its derivatives, as demonstrated by the NMR and fluorescence competition experiments. Furthermore, host 2 is able to act as a fluorescence displacement sensor for discriminating choline, acetylcholine, l-carnitine, and glycine betaine effectively.
Authors:
 [1] ;  [1] ;  [1] ;  [1] ;  [1] ; ORCiD logo [2] ;  [3] ;  [4] ;  [5] ;  [1] ;  [1] ;  [1]
  1. Northwest Univ., Xi'an (China)
  2. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
  3. Institute of Organic and Biochemistry, Prague (Czech Republic); Charles Univ. in Prague, Albertov (Czech Republic)
  4. Institute of Organic Chemistry and Biochemistry, Prague (Czech Republic); Palacky Univ., Olomouc (Czech Republic)
  5. Ben-Gurion Univ. of the Negev, Beer-Sheva (Israel)
Publication Date:
Grant/Contract Number:
AC05-00OR22725
Type:
Accepted Manuscript
Journal Name:
Nature Communications
Additional Journal Information:
Journal Volume: 8; Journal Issue: 1; Journal ID: ISSN 2041-1723
Publisher:
Nature Publishing Group
Research Org:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org:
USDOE
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
OSTI Identifier:
1408031