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

Abstract

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:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1408031
Grant/Contract Number:  
[AC05-00OR22725]
Resource 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
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Jia, Chuandong, Zuo, Wei, Yang, Dong, Chen, Yanming, Cao, Liping, Custelcean, Radu, Hostas, Jiri, Hobza, Pavel, Glaser, Robert, Wang, Yao -Yu, Yang, Xiao -Juan, and Wu, Biao. Selective binding of choline by a phosphate-coordination-based triple helicate featuring an aromatic box. United States: N. p., 2017. Web. doi:10.1038/s41467-017-00915-8.
Jia, Chuandong, Zuo, Wei, Yang, Dong, Chen, Yanming, Cao, Liping, Custelcean, Radu, Hostas, Jiri, Hobza, Pavel, Glaser, Robert, Wang, Yao -Yu, Yang, Xiao -Juan, & Wu, Biao. Selective binding of choline by a phosphate-coordination-based triple helicate featuring an aromatic box. United States. doi:10.1038/s41467-017-00915-8.
Jia, Chuandong, Zuo, Wei, Yang, Dong, Chen, Yanming, Cao, Liping, Custelcean, Radu, Hostas, Jiri, Hobza, Pavel, Glaser, Robert, Wang, Yao -Yu, Yang, Xiao -Juan, and Wu, Biao. Mon . "Selective binding of choline by a phosphate-coordination-based triple helicate featuring an aromatic box". United States. doi:10.1038/s41467-017-00915-8. https://www.osti.gov/servlets/purl/1408031.
@article{osti_1408031,
title = {Selective binding of choline by a phosphate-coordination-based triple helicate featuring an aromatic box},
author = {Jia, Chuandong and Zuo, Wei and Yang, Dong and Chen, Yanming and Cao, Liping and Custelcean, Radu and Hostas, Jiri and Hobza, Pavel and Glaser, Robert and Wang, Yao -Yu and Yang, Xiao -Juan and Wu, Biao},
abstractNote = {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.},
doi = {10.1038/s41467-017-00915-8},
journal = {Nature Communications},
number = [1],
volume = [8],
place = {United States},
year = {2017},
month = {10}
}

Journal Article:
Free Publicly Available Full Text
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Citation Metrics:
Cited by: 12 works
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Figures / Tables:

Fig. 1 Fig. 1: Structure of a ChoX-mimicking triple anion helicate receptor. a Structures of bis-bisurea ligands L1a, L1b, and L2 that can readily form the A2L3 (A= anion, L= ligand) triple helicates when coordinated with PO43− ions. b Crystal structure of complex 1, (TMA)5[(TMA)⊂ (PO4)2(L2)3] (⊂= encapsulated by; only an Mmore » enantiomer is shown; other counter cations, solvent molecules, and non-acidic protons are omitted for clarity); c Hydrogen bonds formed between a PO43− ion and six urea units; d The aromatic box (site-I) trapping a TMA+ through cation–π interactions (purple-dashed lines) and a potential hydrogen-bonding site (II), which together resembles the structure of Ch+⊂ChoX« less

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    • DOI: 10.1021/jacs.6b05897

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      Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.