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

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

doi:10.1038/s41467-017-00915-8

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

Journal Article · Mon Oct 16 00:00:00 EDT 2017 · Nature Communications

DOI:https://doi.org/10.1038/s41467-017-00915-8· OSTI ID:1408031

Jia, Chuandong ^[1]; Zuo, Wei ^[1]; Yang, Dong ^[1]; Chen, Yanming ^[1]; Cao, Liping ^[1];

^[2]; Hostas, Jiri ^[3]; Hobza, Pavel ^[4]; Glaser, Robert ^[5]; Wang, Yao -Yu ^[1]; Yang, Xiao -Juan ^[1]; Wu, Biao ^[1]

Northwest Univ., Xi'an (China)
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Institute of Organic and Biochemistry, Prague (Czech Republic); Charles Univ. in Prague, Albertov (Czech Republic)
Institute of Organic Chemistry and Biochemistry, Prague (Czech Republic); Palacky Univ., Olomouc (Czech Republic)
Ben-Gurion Univ. of the Negev, Beer-Sheva (Israel)

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.

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Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1408031

Journal Information:: Nature Communications, Vol. 8, Issue 1; ISSN 2041-1723

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 38 works

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