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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 Laboratory (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. https://doi.org/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. https://doi.org/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 = {Mon Oct 16 00:00:00 EDT 2017},
month = {Mon Oct 16 00:00:00 EDT 2017}
}

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Cited by: 38 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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Works referenced in this record:

Substrate-Selective Supramolecular Tandem Assays: Monitoring Enzyme Inhibition of Arginase and Diamine Oxidase by Fluorescent Dye Displacement from Calixarene and Cucurbituril Macrocycles
journal, August 2009

  • Nau, Werner M.; Ghale, Garima; Hennig, Andreas
  • Journal of the American Chemical Society, Vol. 131, Issue 32
  • DOI: 10.1021/ja904165c

A Synthetic Receptor for Choline and Carnitine
journal, November 2002

  • Ballester, Pablo; Shivanyuk, Alexander; Far, Adel Rafai
  • Journal of the American Chemical Society, Vol. 124, Issue 47
  • DOI: 10.1021/ja0282689

Molecular containers in complex chemical systems
journal, January 2015

  • Zarra, Salvatore; Wood, Daniel M.; Roberts, Derrick A.
  • Chemical Society Reviews, Vol. 44, Issue 2
  • DOI: 10.1039/C4CS00165F

Supramolecular Chemistry
book, January 2009


Organic cage compounds – from shape-persistency to function
journal, January 2014

  • Zhang, Gang; Mastalerz, Michael
  • Chem. Soc. Rev., Vol. 43, Issue 6
  • DOI: 10.1039/C3CS60358J

Atomic structure of acetylcholinesterase from Torpedo californica: a prototypic acetylcholine-binding protein
journal, August 1991


Peripheral Templation Generates an M II 6 L 4 Guest-Binding Capsule
journal, April 2016

  • Rizzuto, Felix J.; Wu, Wen-Yuan; Ronson, Tanya K.
  • Angewandte Chemie International Edition, Vol. 55, Issue 28
  • DOI: 10.1002/anie.201602135

A Triple Anion Helicate Assembled from a Bis(biurea) Ligand and Phosphate Ions
journal, May 2011

  • Li, Shaoguang; Jia, Chuandong; Wu, Biao
  • Angewandte Chemie International Edition, Vol. 50, Issue 25
  • DOI: 10.1002/anie.201180593

Anion recognition by oligo-(thio)urea-based receptors
journal, January 2016

  • Jia, Chuandong; Zuo, Wei; Zhang, Dan
  • Chemical Communications, Vol. 52, Issue 62
  • DOI: 10.1039/C6CC03761E

Metal–organic molecular cages: applications of biochemical implications
journal, January 2015

  • Ahmad, Nazir; Younus, Hussein A.; Chughtai, Adeel H.
  • Chemical Society Reviews, Vol. 44, Issue 1
  • DOI: 10.1039/C4CS00222A

Crystal Structures of the Choline/Acetylcholine Substrate-binding Protein ChoX from Sinorhizobium meliloti in the Liganded and Unliganded-Closed States
journal, September 2008

  • Oswald, Christine; Smits, Sander H. J.; Höing, Marina
  • Journal of Biological Chemistry, Vol. 283, Issue 47
  • DOI: 10.1074/jbc.M806021200

Selective Cavitand-Mediated Endocytosis of Targeted Imaging Agents into Live Cells
journal, April 2013

  • Ghang, Yoo-Jin; Schramm, Michael P.; Zhang, Fan
  • Journal of the American Chemical Society, Vol. 135, Issue 19
  • DOI: 10.1021/ja401273g

A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu
journal, April 2010

  • Grimme, Stefan; Antony, Jens; Ehrlich, Stephan
  • The Journal of Chemical Physics, Vol. 132, Issue 15
  • DOI: 10.1063/1.3382344

Encapsulation of Halocarbons in a Tetrahedral Anion Cage
journal, June 2015

  • Yang, Dong; Zhao, Jie; Zhao, Yanxia
  • Angewandte Chemie International Edition, Vol. 54, Issue 30
  • DOI: 10.1002/anie.201502399

Reinvestigation of Calixarene-Based Artificial-Signaling Acetylcholine Receptors Useful in Neutral Aqueous (Water/Methanol) Solution
journal, January 1996

  • Koh, Kwang Nak; Araki, Koji; Ikeda, Atsushi
  • Journal of the American Chemical Society, Vol. 118, Issue 4
  • DOI: 10.1021/ja951488k

Highly Efficient Extraction of Sulfate Ions with a Tripodal Hexaurea Receptor
journal, December 2010

  • Jia, Chuandong; Wu, Biao; Li, Shaoguang
  • Angewandte Chemie International Edition, Vol. 50, Issue 2
  • DOI: 10.1002/anie.201004461

Kinetically Stable Complexes in Water:  The Role of Hydration and Hydrophobicity
journal, March 2004

  • Biros, Shannon M.; Ullrich, Elke C.; Hof, Fraser
  • Journal of the American Chemical Society, Vol. 126, Issue 9
  • DOI: 10.1021/ja038823m

Stabilization of reactive species by supramolecular encapsulation
journal, January 2016

  • Galan, Albano; Ballester, Pablo
  • Chemical Society Reviews, Vol. 45, Issue 6
  • DOI: 10.1039/C5CS00861A

Tetrahedral Anion Cage: Self-Assembly of a (PO 4 ) 4 L 4 Complex from a Tris(bisurea) Ligand
journal, April 2013

  • Wu, Biao; Cui, Fengjuan; Lei, Yibo
  • Angewandte Chemie International Edition, Vol. 52, Issue 19
  • DOI: 10.1002/anie.201209930

Acetylcholine Detection at Micromolar Concentrations with the Use of an Artificial Receptor-Based Fluorescence Switch
journal, March 2008

  • Korbakov, Nina; Timmerman, Peter; Lidich, Nina
  • Langmuir, Vol. 24, Issue 6
  • DOI: 10.1021/la703010z

Substrate Binding and Catalytic Mechanism of Human Choline Acetyltransferase ,
journal, December 2006

  • Kim, Ae-Ri; Rylett, R. Jane; Shilton, Brian H.
  • Biochemistry, Vol. 45, Issue 49
  • DOI: 10.1021/bi061536l

Applications of Supramolecular Anion Recognition
journal, May 2015


Aromatic Rings in Chemical and Biological Recognition: Energetics and Structures
journal, April 2011

  • Salonen, Laura M.; Ellermann, Manuel; Diederich, François
  • Angewandte Chemie International Edition, Vol. 50, Issue 21
  • DOI: 10.1002/anie.201007560

Chemosensing Ensembles for Monitoring Biomembrane Transport in Real Time
journal, January 2014

  • Ghale, Garima; Lanctôt, Adrienne G.; Kreissl, Hannah T.
  • Angewandte Chemie International Edition, Vol. 53, Issue 10
  • DOI: 10.1002/anie.201309583

Activation of a Water-Soluble Resorcinarene Cavitand at the Water–Phosphocholine Micelle Interface
journal, November 2011

  • Javor, Sacha; Rebek, Julius
  • Journal of the American Chemical Society, Vol. 133, Issue 43
  • DOI: 10.1021/ja2073774

Label-free continuous enzyme assays with macrocycle-fluorescent dye complexes
journal, July 2007

  • Hennig, Andreas; Bakirci, Hüseyin; Nau, Werner M.
  • Nature Methods, Vol. 4, Issue 8
  • DOI: 10.1038/nmeth1064

Anion coordination and anion-templated assembly: Highlights from 2002 to 2004
journal, December 2006


A Nexus between Theory and Experiment: Non-Empirical Quantum Mechanical Computational Methodology Applied to Cucurbit[ n ]uril⋅Guest Binding Interactions
journal, October 2016

  • Hostaš, Jiří; Sigwalt, David; Šekutor, Marina
  • Chemistry - A European Journal, Vol. 22, Issue 48
  • DOI: 10.1002/chem.201601833

Catalytic Ammonia Synthesis in Homogeneous Solution-Biomimetic at Last?
journal, November 2013

  • Broda, Henning; Tuczek, Felix
  • Angewandte Chemie International Edition, Vol. 53, Issue 3
  • DOI: 10.1002/anie.201308780

Pillararenes, A New Class of Macrocycles for Supramolecular Chemistry
journal, May 2012

  • Xue, Min; Yang, Yong; Chi, Xiaodong
  • Accounts of Chemical Research, Vol. 45, Issue 8
  • DOI: 10.1021/ar2003418

Operational calixarene-based fluorescent sensing systems for choline and acetylcholine and their application to enzymatic reactions
journal, January 2011

  • Guo, Dong-Sheng; Uzunova, Vanya D.; Su, Xin
  • Chemical Science, Vol. 2, Issue 9
  • DOI: 10.1039/c1sc00231g

Acetylcholine binding by a synthetic receptor: implications for biological recognition
journal, December 1990


The Cation−π Interaction
journal, August 1997

  • Ma, Jennifer C.; Dougherty, Dennis A.
  • Chemical Reviews, Vol. 97, Issue 5
  • DOI: 10.1021/cr9603744

Acid Catalysis in Basic Solution: A Supramolecular Host Promotes Orthoformate Hydrolysis
journal, April 2007


Interactions with Aromatic Rings in Chemical and Biological Recognition
journal, March 2003

  • Meyer, Emmanuel A.; Castellano, Ronald K.; Diederich, François
  • Angewandte Chemie International Edition, Vol. 42, Issue 11
  • DOI: 10.1002/anie.200390319

Supramolecular Chemistry—Scope and Perspectives Molecules, Supermolecules, and Molecular Devices(Nobel Lecture)
journal, January 1988

  • Lehn, Jean-Marie
  • Angewandte Chemie International Edition in English, Vol. 27, Issue 1
  • DOI: 10.1002/anie.198800891

The Effect of the Spacer of Bis(biurea) Ligands on the Structure of A 2 L 3 -type (A=anion) Phosphate Complexes
journal, December 2014

  • Wu, Biao; Li, Shaoguang; Lei, Yibo
  • Chemistry - A European Journal, Vol. 21, Issue 6
  • DOI: 10.1002/chem.201405235

A supramolecular microenvironment strategy for transition metal catalysis
journal, December 2015


A Hemicyanine-Conjugated Copolymer as a Highly Sensitive Fluorescent Thermometer
journal, April 2008

  • Shiraishi, Yasuhiro; Miyamoto, Ryo; Hirai, Takayuki
  • Langmuir, Vol. 24, Issue 8
  • DOI: 10.1021/la703890n

EQNMR: a computer program for the calculation of stability constants from nuclear magnetic resonance chemical shift data
journal, January 1993

  • Hynes, Michael J.
  • Journal of the Chemical Society, Dalton Transactions, Issue 2
  • DOI: 10.1039/dt9930000311

Highly efficient catalysis of the Kemp elimination in the cavity of a cubic coordination cage
journal, February 2016

  • Cullen, William; Misuraca, M. Cristina; Hunter, Christopher A.
  • Nature Chemistry, Vol. 8, Issue 3
  • DOI: 10.1038/nchem.2452

Self-Aggregating Deep Cavitand Acts as a Fluorescence Displacement Sensor for Lysine Methylation
journal, August 2016

  • Liu, Yang; Perez, Lizeth; Mettry, Magi
  • Journal of the American Chemical Society, Vol. 138, Issue 34
  • DOI: 10.1021/jacs.6b05897

Molecular containers assembled through the hydrophobic effect
journal, January 2015

  • Jordan, Jacobs H.; Gibb, Bruce C.
  • Chemical Society Reviews, Vol. 44, Issue 2
  • DOI: 10.1039/C4CS00191E

Tetra-phosphonate Calix[4]pyrrole Cavitands as Multitopic Receptors for the Recognition of Ion Pairs
journal, January 2015

  • Ciardi, Moira; Galán, Albano; Ballester, Pablo
  • Journal of the American Chemical Society, Vol. 137, Issue 5
  • DOI: 10.1021/ja512590j

Calixarene-based supramolecular polymerization in solution
journal, January 2012

  • Guo, Dong-Sheng; Liu, Yu
  • Chemical Society Reviews, Vol. 41, Issue 18
  • DOI: 10.1039/c2cs35075k

A supramolecular approach to combining enzymatic and transition metal catalysis
journal, January 2013

  • Wang, Z. Jane; Clary, Kristen N.; Bergman, Robert G.
  • Nature Chemistry, Vol. 5, Issue 2
  • DOI: 10.1038/nchem.1531

Antibody-Free Reading of the Histone Code Using a Simple Chemical Sensor Array
journal, July 2012

  • Minaker, Samuel A.; Daze, Kevin D.; Ma, Manuel C. F.
  • Journal of the American Chemical Society, Vol. 134, Issue 28
  • DOI: 10.1021/ja303465x

Acetylcholine Recognition by a Deep, Biomimetic Pocket
journal, July 2003

  • Hof, Fraser; Trembleau, Laurent; Ullrich, Elke Christine
  • Angewandte Chemie International Edition, Vol. 42, Issue 27
  • DOI: 10.1002/anie.200351174

Crystalline molecular flasks
journal, April 2011

  • Inokuma, Yasuhide; Kawano, Masaki; Fujita, Makoto
  • Nature Chemistry, Vol. 3, Issue 5
  • DOI: 10.1038/nchem.1031

Amide-Based Ligands for Anion Coordination
journal, December 2006

  • Kang, Sung Ok; Begum, Rowshan Ara; Bowman-James, Kristin
  • Angewandte Chemie International Edition, Vol. 45, Issue 47
  • DOI: 10.1002/anie.200602006

Program DYNAFIT for the Analysis of Enzyme Kinetic Data: Application to HIV Proteinase
journal, June 1996


Supermolecules by Design
journal, November 1999

  • Caulder, Dana L.; Raymond, Kenneth N.
  • Accounts of Chemical Research, Vol. 32, Issue 11
  • DOI: 10.1021/ar970224v

Molecular paneling via coordination
journal, January 2001

  • Fujita, Makoto; Umemoto, Kazuhiko; Yoshizawa, Michito
  • Chemical Communications, Issue 6
  • DOI: 10.1039/b008684n

Binding Mechanisms in Supramolecular Complexes
journal, May 2009

  • Schneider, Hans-Jörg
  • Angewandte Chemie International Edition, Vol. 48, Issue 22
  • DOI: 10.1002/anie.200802947

A Triple Anion Helicate Assembled from a Bis(biurea) Ligand and Phosphate Ions
journal, May 2011


Encapsulation of Halocarbons in a Tetrahedral Anion Cage
journal, June 2015


Tetrahedral Anion Cage: Self-Assembly of a (PO 4 ) 4 L 4 Complex from a Tris(bisurea) Ligand
journal, April 2013


Supramolecular Chemistry
journal, January 2002


Peripheral Templation Generates an M II 6 L 4 Guest-Binding Capsule
journal, April 2016

  • Rizzuto, Felix J.; Wu, Wen-Yuan; Ronson, Tanya K.
  • Angewandte Chemie, Vol. 128, Issue 28
  • DOI: 10.1002/ange.201602135

Interactions with Aromatic Rings in Chemical and Biological Recognition
journal, September 2003

  • Meyer, Emmanuel A.; Castellano, Ronald K.; Diederich, François
  • Angewandte Chemie International Edition, Vol. 42, Issue 35
  • DOI: 10.1002/anie.200390574

Supramolecular Chemistry
journal, December 1999


Highly Efficient Extraction of Sulfate Ions with a Tripodal Hexaurea Receptor
journal, December 2010


A Triple Anion Helicate Assembled from a Bis(biurea) Ligand and Phosphate Ions
journal, May 2011


Interactions with Aromatic Rings in Chemical and Biological Recognition.
journal, June 2003

  • Meyer, Emmanuel A.; Castellano, Ronald K.; Diederich, Francois
  • ChemInform, Vol. 34, Issue 22
  • DOI: 10.1002/chin.200322285

Amide-Based Ligands for Anion Coordination
journal, March 2007

  • Kang, Sung Ok; Begum, Rowshan Ara; Bowman-James, Kristin
  • ChemInform, Vol. 38, Issue 12
  • DOI: 10.1002/chin.200712244

Highly Efficient Extraction of Sulfate Ions with a Tripodal Hexaurea Receptor
journal, December 2010


A Triple Anion Helicate Assembled from a Bis(biurea) Ligand and Phosphate Ions
journal, May 2011


Supramolecular Chemistry—Scope and Perspectives Molecules, Supermolecules, and Molecular Devices(Nobel Lecture)
journal, January 1988

  • Lehn, Jean-Marie
  • Angewandte Chemie International Edition in English, Vol. 27, Issue 1
  • DOI: 10.1002/anie.198800891

Acetylcholine Recognition by a Deep, Biomimetic Pocket
journal, July 2003

  • Hof, Fraser; Trembleau, Laurent; Ullrich, Elke Christine
  • Angewandte Chemie International Edition, Vol. 42, Issue 27
  • DOI: 10.1002/anie.200351174

Interactions with Aromatic Rings in Chemical and Biological Recognition
journal, March 2003

  • Meyer, Emmanuel A.; Castellano, Ronald K.; Diederich, François
  • Angewandte Chemie International Edition, Vol. 42, Issue 11
  • DOI: 10.1002/anie.200390319

Amide-Based Ligands for Anion Coordination
journal, December 2006

  • Kang, Sung Ok; Begum, Rowshan Ara; Bowman-James, Kristin
  • Angewandte Chemie International Edition, Vol. 45, Issue 47
  • DOI: 10.1002/anie.200602006

Binding Mechanisms in Supramolecular Complexes
journal, May 2009

  • Schneider, Hans-Jörg
  • Angewandte Chemie International Edition, Vol. 48, Issue 22
  • DOI: 10.1002/anie.200802947

Aromatic Rings in Chemical and Biological Recognition: Energetics and Structures
journal, April 2011

  • Salonen, Laura M.; Ellermann, Manuel; Diederich, François
  • Angewandte Chemie International Edition, Vol. 50, Issue 21
  • DOI: 10.1002/anie.201007560

Catalytic Ammonia Synthesis in Homogeneous Solution-Biomimetic at Last?
journal, November 2013

  • Broda, Henning; Tuczek, Felix
  • Angewandte Chemie International Edition, Vol. 53, Issue 3
  • DOI: 10.1002/anie.201308780

Chemosensing Ensembles for Monitoring Biomembrane Transport in Real Time
journal, January 2014

  • Ghale, Garima; Lanctôt, Adrienne G.; Kreissl, Hannah T.
  • Angewandte Chemie International Edition, Vol. 53, Issue 10
  • DOI: 10.1002/anie.201309583

Encapsulation of Halocarbons in a Tetrahedral Anion Cage
journal, June 2015

  • Yang, Dong; Zhao, Jie; Zhao, Yanxia
  • Angewandte Chemie International Edition, Vol. 54, Issue 30
  • DOI: 10.1002/anie.201502399

The Effect of the Spacer of Bis(biurea) Ligands on the Structure of A 2 L 3 -type (A=anion) Phosphate Complexes
journal, December 2014

  • Wu, Biao; Li, Shaoguang; Lei, Yibo
  • Chemistry - A European Journal, Vol. 21, Issue 6
  • DOI: 10.1002/chem.201405235

A Nexus between Theory and Experiment: Non-Empirical Quantum Mechanical Computational Methodology Applied to Cucurbit[ n ]uril⋅Guest Binding Interactions
journal, October 2016

  • Hostaš, Jiří; Sigwalt, David; Šekutor, Marina
  • Chemistry - A European Journal, Vol. 22, Issue 48
  • DOI: 10.1002/chem.201601833

Program DYNAFIT for the Analysis of Enzyme Kinetic Data: Application to HIV Proteinase
journal, June 1996


Anion coordination and anion-templated assembly: Highlights from 2002 to 2004
journal, December 2006


Applications of Supramolecular Anion Recognition
journal, May 2015


Supermolecules by Design
journal, November 1999

  • Caulder, Dana L.; Raymond, Kenneth N.
  • Accounts of Chemical Research, Vol. 32, Issue 11
  • DOI: 10.1021/ar970224v

A Synthetic Receptor for Choline and Carnitine
journal, November 2002

  • Ballester, Pablo; Shivanyuk, Alexander; Far, Adel Rafai
  • Journal of the American Chemical Society, Vol. 124, Issue 47
  • DOI: 10.1021/ja0282689

Kinetically Stable Complexes in Water:  The Role of Hydration and Hydrophobicity
journal, March 2004

  • Biros, Shannon M.; Ullrich, Elke C.; Hof, Fraser
  • Journal of the American Chemical Society, Vol. 126, Issue 9
  • DOI: 10.1021/ja038823m

Activation of a Water-Soluble Resorcinarene Cavitand at the Water–Phosphocholine Micelle Interface
journal, November 2011

  • Javor, Sacha; Rebek, Julius
  • Journal of the American Chemical Society, Vol. 133, Issue 43
  • DOI: 10.1021/ja2073774

Antibody-Free Reading of the Histone Code Using a Simple Chemical Sensor Array
journal, July 2012

  • Minaker, Samuel A.; Daze, Kevin D.; Ma, Manuel C. F.
  • Journal of the American Chemical Society, Vol. 134, Issue 28
  • DOI: 10.1021/ja303465x

Tetra-phosphonate Calix[4]pyrrole Cavitands as Multitopic Receptors for the Recognition of Ion Pairs
journal, January 2015

  • Ciardi, Moira; Galán, Albano; Ballester, Pablo
  • Journal of the American Chemical Society, Vol. 137, Issue 5
  • DOI: 10.1021/ja512590j

Substrate-Selective Supramolecular Tandem Assays: Monitoring Enzyme Inhibition of Arginase and Diamine Oxidase by Fluorescent Dye Displacement from Calixarene and Cucurbituril Macrocycles
journal, August 2009

  • Nau, Werner M.; Ghale, Garima; Hennig, Andreas
  • Journal of the American Chemical Society, Vol. 131, Issue 32
  • DOI: 10.1021/ja904165c

Reinvestigation of Calixarene-Based Artificial-Signaling Acetylcholine Receptors Useful in Neutral Aqueous (Water/Methanol) Solution
journal, January 1996

  • Koh, Kwang Nak; Araki, Koji; Ikeda, Atsushi
  • Journal of the American Chemical Society, Vol. 118, Issue 4
  • DOI: 10.1021/ja951488k

Acetylcholine Detection at Micromolar Concentrations with the Use of an Artificial Receptor-Based Fluorescence Switch
journal, March 2008

  • Korbakov, Nina; Timmerman, Peter; Lidich, Nina
  • Langmuir, Vol. 24, Issue 6
  • DOI: 10.1021/la703010z

A Hemicyanine-Conjugated Copolymer as a Highly Sensitive Fluorescent Thermometer
journal, April 2008

  • Shiraishi, Yasuhiro; Miyamoto, Ryo; Hirai, Takayuki
  • Langmuir, Vol. 24, Issue 8
  • DOI: 10.1021/la703890n

Crystalline molecular flasks
journal, April 2011

  • Inokuma, Yasuhide; Kawano, Masaki; Fujita, Makoto
  • Nature Chemistry, Vol. 3, Issue 5
  • DOI: 10.1038/nchem.1031

A supramolecular approach to combining enzymatic and transition metal catalysis
journal, January 2013

  • Wang, Z. Jane; Clary, Kristen N.; Bergman, Robert G.
  • Nature Chemistry, Vol. 5, Issue 2
  • DOI: 10.1038/nchem.1531

Highly efficient catalysis of the Kemp elimination in the cavity of a cubic coordination cage
journal, February 2016

  • Cullen, William; Misuraca, M. Cristina; Hunter, Christopher A.
  • Nature Chemistry, Vol. 8, Issue 3
  • DOI: 10.1038/nchem.2452

Label-free continuous enzyme assays with macrocycle-fluorescent dye complexes
journal, July 2007

  • Hennig, Andreas; Bakirci, Hüseyin; Nau, Werner M.
  • Nature Methods, Vol. 4, Issue 8
  • DOI: 10.1038/nmeth1064

Self-assembled capsules based on tetrafunctionalized calix[4]resorcinarene cavitands
journal, January 2015

  • Kobayashi, Kenji; Yamanaka, Masamichi
  • Chemical Society Reviews, Vol. 44, Issue 2
  • DOI: 10.1039/c4cs00153b

A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu
journal, April 2010

  • Grimme, Stefan; Antony, Jens; Ehrlich, Stephan
  • The Journal of Chemical Physics, Vol. 132, Issue 15
  • DOI: 10.1063/1.3382344

Acid Catalysis in Basic Solution: A Supramolecular Host Promotes Orthoformate Hydrolysis
journal, April 2007


Atomic structure of acetylcholinesterase from Torpedo californica: a prototypic acetylcholine-binding protein
journal, August 1991


Acetylcholine binding by a synthetic receptor: implications for biological recognition
journal, December 1990


The Sinorhizobium meliloti ABC Transporter Cho Is Highly Specific for Choline and Expressed in Bacteroids from Medicago sativa Nodules
journal, September 2004


Works referencing / citing this record:

Multivalent Crown Ether Receptors Enable Allosteric Regulation of Anion Exchange in an Fe 4 L 6 Tetrahedron
journal, September 2018

  • von Krbek, Larissa K. S.; Roberts, Derrick A.; Pilgrim, Ben S.
  • Angewandte Chemie, Vol. 130, Issue 43
  • DOI: 10.1002/ange.201808534

A Long‐Lived Halogen‐Bonding Anion Triple Helicate Accommodates Rapid Guest Exchange
journal, October 2018

  • Massena, Casey J.; Decato, Daniel A.; Berryman, Orion B.
  • Angewandte Chemie, Vol. 130, Issue 49
  • DOI: 10.1002/ange.201810415

Peripheral Templation-Modulated Interconversion between an A 4 L 6 Tetrahedral Anion Cage and A 2 L 3 Triple Helicate with Guest Capture/Release
journal, January 2018

  • Bai, Xuemin; Jia, Chuandong; Zhao, Yanxia
  • Angewandte Chemie International Edition, Vol. 57, Issue 7
  • DOI: 10.1002/anie.201712080

Multivalent Crown Ether Receptors Enable Allosteric Regulation of Anion Exchange in an Fe 4 L 6 Tetrahedron
journal, September 2018

  • von Krbek, Larissa K. S.; Roberts, Derrick A.; Pilgrim, Ben S.
  • Angewandte Chemie International Edition, Vol. 57, Issue 43
  • DOI: 10.1002/anie.201808534

A Long-Lived Halogen-Bonding Anion Triple Helicate Accommodates Rapid Guest Exchange
journal, November 2018

  • Massena, Casey J.; Decato, Daniel A.; Berryman, Orion B.
  • Angewandte Chemie International Edition, Vol. 57, Issue 49
  • DOI: 10.1002/anie.201810415

Majority-Rules Effect and Allostery in Molecular Recognition of Calix[4]arene-Based Triple-Stranded Metallohelicates
journal, June 2018

  • Yamasaki, Yutaro; Shio, Hidemi; Amimoto, Tomoko
  • Chemistry - A European Journal, Vol. 24, Issue 34
  • DOI: 10.1002/chem.201800997

Anion‐Coordination‐Assisted Assembly of Supramolecular Charge‐Transfer Complexes Based on Tris(urea) Ligands
journal, January 2020

  • Zhang, Dan; Hou, Le‐Kai; Zhang, Qiang
  • Chemistry – A European Journal, Vol. 26, Issue 6
  • DOI: 10.1002/chem.201905021

Anion-coordination-directed self-assemblies
journal, January 2018

  • Yang, Dong; Zhao, Jie; Yang, Xiao-Juan
  • Organic Chemistry Frontiers, Vol. 5, Issue 4
  • DOI: 10.1039/c7qo00895c

Chirality sensing of choline derivatives by a triple anion helicate cage through induced circular dichroism
journal, January 2018

  • Zuo, Wei; Huang, Zhe; Zhao, Yanxia
  • Chemical Communications, Vol. 54, Issue 53
  • DOI: 10.1039/c8cc03883j

Selective recognition of choline phosphate by tripodal hexa-urea receptors with dual binding sites: crystal and solution evidence
journal, January 2019

  • Zuo, Wei; Jia, Chuandong; Zhang, Huizheng
  • Chemical Science, Vol. 10, Issue 8
  • DOI: 10.1039/c8sc04338h

Chirality transcription in the anion-coordination-driven assembly of tetrahedral cages
journal, January 2020

  • Fu, Jin; Zheng, Bo; Zhang, Huizheng
  • Chemical Communications, Vol. 56, Issue 16
  • DOI: 10.1039/c9cc09752j

Selective recognition of acetylcholine over choline by a fluorescent cage
journal, January 2019

  • Long, Augustin; Fantozzi, Nicolas; Pinet, Sandra
  • Organic & Biomolecular Chemistry, Vol. 17, Issue 21
  • DOI: 10.1039/c9ob00931k

Construction and interconversion of anion-coordination-based (‘aniono’) grids and double helicates modulated by counter-cations
journal, January 2019

  • Fan, Xiaoxia; Zhang, Dan; Jiang, Shiyu
  • Chemical Science, Vol. 10, Issue 25
  • DOI: 10.1039/c9sc02012h

Selective recognition of choline phosphate by tripodal hexa-urea receptors with dual binding sites: crystal and solution evidence
journal, January 2019

  • Zuo, Wei; Jia, Chuandong; Zhang, Huizheng
  • Chemical Science, Vol. 10, Issue 8
  • DOI: 10.1039/c8sc04338h

Construction and interconversion of anion-coordination-based (‘aniono’) grids and double helicates modulated by counter-cations
journal, January 2019

  • Fan, Xiaoxia; Zhang, Dan; Jiang, Shiyu
  • Chemical Science, Vol. 10, Issue 25
  • DOI: 10.1039/c9sc02012h

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