Selective binding of (thio)sulfate and phosphate in water by quaternary ammonium functionalized oligo-ureas
Abstract
Recognition of (thio)sulfate and phosphate in aqueous solutions has been demonstrated by using oligo-urea-based receptors functionalized with quaternary ammonium groups. The ammonium groups allow for increased aqueous solubility while simultaneously providing positive coulombic interactions and stronger hydrogen bonding through an inductive effect. This simple and generally applicable modification provides an effective way to bolster the anion binding and water solubility of oligo-urea-based receptors. Finally, with a water soluble receptor 2, selective binding of adenosine phosphates was achieved at physiological pH.
- Authors:
-
- Northwest Univ., Xi’an (China). Key Lab. of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry and Materials Science
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Chemical Sciences Division
- Publication Date:
- Research Org.:
- Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1492147
- Alternate Identifier(s):
- OSTI ID: 1491430
- Grant/Contract Number:
- AC05-00OR22725
- Resource Type:
- Accepted Manuscript
- Journal Name:
- ChemComm
- Additional Journal Information:
- Journal Volume: 55; Journal Issue: 12; Journal ID: ISSN 1359-7345
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Huang, Zhe, Jia, Chuandong, Wu, Biao, Jansone-Popova, Santa, Seipp, Charles A., and Custelcean, Radu. Selective binding of (thio)sulfate and phosphate in water by quaternary ammonium functionalized oligo-ureas. United States: N. p., 2019.
Web. doi:10.1039/c8cc09550g.
Huang, Zhe, Jia, Chuandong, Wu, Biao, Jansone-Popova, Santa, Seipp, Charles A., & Custelcean, Radu. Selective binding of (thio)sulfate and phosphate in water by quaternary ammonium functionalized oligo-ureas. United States. https://doi.org/10.1039/c8cc09550g
Huang, Zhe, Jia, Chuandong, Wu, Biao, Jansone-Popova, Santa, Seipp, Charles A., and Custelcean, Radu. Mon .
"Selective binding of (thio)sulfate and phosphate in water by quaternary ammonium functionalized oligo-ureas". United States. https://doi.org/10.1039/c8cc09550g. https://www.osti.gov/servlets/purl/1492147.
@article{osti_1492147,
title = {Selective binding of (thio)sulfate and phosphate in water by quaternary ammonium functionalized oligo-ureas},
author = {Huang, Zhe and Jia, Chuandong and Wu, Biao and Jansone-Popova, Santa and Seipp, Charles A. and Custelcean, Radu},
abstractNote = {Recognition of (thio)sulfate and phosphate in aqueous solutions has been demonstrated by using oligo-urea-based receptors functionalized with quaternary ammonium groups. The ammonium groups allow for increased aqueous solubility while simultaneously providing positive coulombic interactions and stronger hydrogen bonding through an inductive effect. This simple and generally applicable modification provides an effective way to bolster the anion binding and water solubility of oligo-urea-based receptors. Finally, with a water soluble receptor 2, selective binding of adenosine phosphates was achieved at physiological pH.},
doi = {10.1039/c8cc09550g},
journal = {ChemComm},
number = 12,
volume = 55,
place = {United States},
year = {Mon Jan 14 00:00:00 EST 2019},
month = {Mon Jan 14 00:00:00 EST 2019}
}
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Works referenced in this record:
Fluorescent and colorimetric sensors for anionic species
journal, January 2018
- Gale, Philip A.; Caltagirone, Claudia
- Coordination Chemistry Reviews, Vol. 354
Recent advances in molecular recognition in water: artificial receptors and supramolecular catalysis
journal, January 2014
- Kataev, Evgeny A.; Müller, Christoph
- Tetrahedron, Vol. 70, Issue 2
Urea-Functionalized M 4 L 6 Cage Receptors: Anion-Templated Self-Assembly and Selective Guest Exchange in Aqueous Solutions
journal, May 2012
- Custelcean, Radu; Bonnesen, Peter V.; Duncan, Nathan C.
- Journal of the American Chemical Society, Vol. 134, Issue 20
A Cyclopeptide-Derived Molecular Cage for Sulfate Ions That Closes with a Click
journal, May 2010
- Fiehn, Thomas; Goddard, Richard; Seidel, Rüdiger W.
- Chemistry - A European Journal, Vol. 16, Issue 24
Receptors for tetrahedral oxyanions
journal, December 2006
- Katayev, Evgeny A.; Ustynyuk, Yuri A.; Sessler, Jonathan L.
- Coordination Chemistry Reviews, Vol. 250, Issue 23-24
Alkylation of amines. New method for the synthesis of quaternary ammonium compounds from primary and secondary amines
journal, May 1970
- Sommer, Harold Z.; Jackson, Larry L.
- The Journal of Organic Chemistry, Vol. 35, Issue 5
Highly Selective Fluorescent Recognition of Sulfate in Water by Two Rigid Tetrakisimidazolium Macrocycles with Peripheral Chains
journal, September 2013
- Zhou, Hongjun; Zhao, Yinsong,; Gao, Ge
- Journal of the American Chemical Society, Vol. 135, Issue 40
Amino acid containing anion receptors
journal, January 2009
- Kubik, Stefan
- Chem. Soc. Rev., Vol. 38, Issue 2
Anion Recognition in Water: Recent Advances from a Supramolecular and Macromolecular Perspective
journal, November 2015
- Langton, Matthew J.; Serpell, Christopher J.; Beer, Paul D.
- Angewandte Chemie International Edition, Vol. 55, Issue 6
Abiotic guanidinium containing receptors for anionic species
journal, May 2003
- Best, Michael D.; Tobey, Suzanne L.; Anslyn, Eric V.
- Coordination Chemistry Reviews, Vol. 240, Issue 1-2
Ionic Self-Assembly of Ammonium-Based Amphiphiles and Negatively Charged Bodipy and Porphyrin Luminophores
journal, March 2007
- Camerel, Franck; Ulrich, Gilles; Barberá, Joaquín
- Chemistry - A European Journal, Vol. 13, Issue 8
Artificial Receptors for the Recognition of Phosphorylated Molecules
journal, November 2011
- Hargrove, Amanda E.; Nieto, Sonia; Zhang, Tianzhi
- Chemical Reviews, Vol. 111, Issue 11
Sulphane sulphur in biological systems: a possible regulatory role
journal, December 1989
- Toohey, J. I.
- Biochemical Journal, Vol. 264, Issue 3
Effects of Solvent Properties on the Anion Binding of Neutral Water-Soluble Bis(cyclopeptides) in Water and Aqueous Solvent Mixtures
journal, July 2017
- Sommer, Fabian; Marcus, Yizhak; Kubik, Stefan
- ACS Omega, Vol. 2, Issue 7
Anion recognition by oligo-(thio)urea-based receptors
journal, January 2016
- Jia, Chuandong; Zuo, Wei; Zhang, Dan
- Chemical Communications, Vol. 52, Issue 62
Supramolecular Chemistry in Water
journal, March 2007
- Oshovsky, Gennady V.; Reinhoudt, David N.; Verboom, Willem
- Angewandte Chemie International Edition, Vol. 46, Issue 14
Physiological Roles and Regulation of Mammalian Sulfate Transporters
journal, January 2001
- Markovich, Daniel
- Physiological Reviews, Vol. 81, Issue 4
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
Aqueous Sulfate Separation by Crystallization of Sulfate-Water Clusters
journal, August 2015
- Custelcean, Radu; Williams, Neil J.; Seipp, Charles A.
- Angewandte Chemie International Edition, Vol. 54, Issue 36
Ammonium based anion receptors
journal, May 2003
- Llinares, José M.; Powell, Douglas; Bowman-James, Kristin
- Coordination Chemistry Reviews, Vol. 240, Issue 1-2
Selectivity Principles in Anion Separation by Crystallization of Hydrogen-Bonding Capsules
journal, May 2010
- Custelcean, Radu; Bock, Aurelien; Moyer, Bruce A.
- Journal of the American Chemical Society, Vol. 132, Issue 20
Anion binding with urea and thiourea derivatives
journal, July 2015
- Blažek Bregović, Vesna; Basarić, Nikola; Mlinarić-Majerski, Kata
- Coordination Chemistry Reviews, Vol. 295
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
Anion recognition in water
journal, January 2010
- Kubik, Stefan
- Chemical Society Reviews, Vol. 39, Issue 10
Moderate and Advanced Intramolecular Proton Transfer in Urea-Anion Hydrogen-Bonded Complexes
journal, July 2011
- Baggi, Giorgio; Boiocchi, Massimo; Fabbrizzi, Luigi
- Chemistry - A European Journal, Vol. 17, Issue 34
Surprisingly selective sulfate extraction by a simple monofunctional di(imino)guanidinium micelle-forming anion receptor
journal, January 2018
- Williams, Neil J.; Seipp, Charles A.; Garrabrant, Kathleen A.
- Chemical Communications, Vol. 54, Issue 72
Selectivity for dinegative versus mononegative oxoanionic guests within a cryptand host
journal, January 2001
- Maubert, Beatrice M.; Nelson, Jane; McKee, Vickie
- Journal of the Chemical Society, Dalton Transactions, Issue 9
Sodium Sulfate Separation from Aqueous Alkaline Solutions via Crystalline Urea-Functionalized Capsules: Thermodynamics and Kinetics of Crystallization
journal, December 2014
- Custelcean, Radu; Sloop, Frederick V.; Rajbanshi, Arbin
- Crystal Growth & Design, Vol. 15, Issue 1
Anion coordination chemistry: From recognition to supramolecular assembly
journal, January 2019
- Zhao, Jie; Yang, Dong; Yang, Xiao-Juan
- Coordination Chemistry Reviews, Vol. 378
A fully complementary, high-affinity receptor for phosphate and sulfate based on an acyclic tris(urea) scaffold
journal, January 2010
- Jia, Chuandong; Wu, Biao; Li, Shaoguang
- Chemical Communications, Vol. 46, Issue 29
A Pyrrolyl-Based Triazolophane: A Macrocyclic Receptor With CH and NH Donor Groups That Exhibits a Preference for Pyrophosphate Anions
journal, October 2010
- Sessler, Jonathan L.; Cai, Jiajia; Gong, Han-Yuan
- Journal of the American Chemical Society, Vol. 132, Issue 40
A Case for Molecular Recognition in Nuclear Separations: Sulfate Separation from Nuclear Wastes
journal, June 2012
- Moyer, Bruce A.; Custelcean, Radu; Hay, Benjamin P.
- Inorganic Chemistry, Vol. 52, Issue 7
Chloride Coordination by Oligoureas: From Mononuclear Crescents to Dinuclear Foldamers
journal, January 2012
- Wu, Biao; Jia, Chuandong; Wang, Xiaolei
- Organic Letters, Vol. 14, Issue 3
Artificial Organic Host Molecules for Anions
journal, August 1997
- Schmidtchen, Franz P.; Berger, Michael
- Chemical Reviews, Vol. 97, Issue 5
Anion-Anion Proton Transfer in Hydrogen Bonded Complexes
journal, March 2010
- Gale, Philip A.; Hiscock, Jennifer R.; Moore, Stephen J.
- Chemistry - An Asian Journal, Vol. 5, Issue 3
Bipyrrole-Strapped Calix[4]pyrroles: Strong Anion Receptors That Extract the Sulfate Anion
journal, October 2014
- Kim, Sung Kuk; Lee, Juhoon; Williams, Neil J.
- Journal of the American Chemical Society, Vol. 136, Issue 42
Applications of Supramolecular Anion Recognition
journal, May 2015
- Busschaert, Nathalie; Caltagirone, Claudia; Van Rossom, Wim
- Chemical Reviews, Vol. 115, Issue 15
Selective Sensing of Sulfate in Aqueous Solution Using a Fluorescent Bis(cyclopeptide)
journal, December 2007
- Reyheller, Carsten; Kubik, Stefan
- Organic Letters, Vol. 9, Issue 25
Dynamic combinatorial development of a neutral synthetic receptor that binds sulfate with nanomolar affinity in aqueous solution
journal, January 2011
- Rodriguez-Docampo, Zaida; Eugenieva-Ilieva, Eugenia; Reyheller, Carsten
- Chemical Communications, Vol. 47, Issue 35
Noncovalent Interactions within a Synthetic Receptor Can Reinforce Guest Binding
journal, August 2006
- Rodriguez-Docampo, Zaida; Pascu, Sofia I.; Kubik, Stefan
- Journal of the American Chemical Society, Vol. 128, Issue 34
Dinuclear Chloride-Binding Foldamers Based on Fluorescent Oligoureas: Dinuclear Chloride-Binding Foldamers
journal, April 2013
- Yang, Peiju; Wang, Jiamin; Jia, Chuandong
- European Journal of Organic Chemistry, Vol. 2013, Issue 17
Preparation and crystal structure of the unusual double-helical copper(I) complex bis(2,6-bis(1-methylbenzimidazol-2-yl)pyridine)dicopper(I) naphthalene-1,5-disulfonate
journal, July 1989
- Piguet, Claude; Bernardinelli, Gerald; Williams, Alan F.
- Inorganic Chemistry, Vol. 28, Issue 15
Anion coordination chemistry in aqueous solution of polyammonium receptors
journal, December 2006
- García-España, Enrique; Díaz, Pilar; Llinares, José M.
- Coordination Chemistry Reviews, Vol. 250, Issue 23-24
Computer-Aided Design of a Sulfate-Encapsulating Receptor
journal, May 2009
- Custelcean, Radu; Bosano, Jerome; Bonnesen, Peter V.
- Angewandte Chemie International Edition, Vol. 48, Issue 22
Tetraureas versus Triureas in Sulfate Binding
journal, December 2010
- Jia, Chuandong; Wu, Biao; Li, Shaoguang
- Organic Letters, Vol. 12, Issue 24
Aqueous Sulfate Separation by Sequestration of [(SO 4 ) 2 (H 2 O) 4 ] 4− Clusters within Highly Insoluble Imine-Linked Bis-Guanidinium Crystals
journal, December 2015
- Custelcean, Radu; Williams, Neil J.; Seipp, Charles A.
- Chemistry - A European Journal, Vol. 22, Issue 6
Anion Receptor Chemistry
journal, September 2016
- Gale, Philip A.; Howe, Ethan N. W.; Wu, Xin
- Chem, Vol. 1, Issue 3
Chelate effects in sulfate binding by amide/urea-based ligands
journal, January 2015
- Jia, Chuandong; Wang, Qi-Qiang; Begum, Rowshan Ara
- Organic & Biomolecular Chemistry, Vol. 13, Issue 25
Halogen bonding in water results in enhanced anion recognition in acyclic and rotaxane hosts
journal, November 2014
- Langton, Matthew J.; Robinson, Sean W.; Marques, Igor
- Nature Chemistry, Vol. 6, Issue 12
Dinegative tetrahedral oxoanion complexation; structural and solution phase observations
journal, January 2004
- Nelson, Jane; Nieuwenhuyzen, Mark; Pál, Ibolya
- Dalton Trans., Issue 15
The role of the Golgi Complex in Sulfate Metabolism
journal, April 1973
- Young, R. W.
- The Journal of Cell Biology, Vol. 57, Issue 1
Aqueous Sulfate Separation by Crystallization of Sulfate-Water Clusters
journal, August 2015
- Custelcean, Radu; Williams, Neil J.; Seipp, Charles A.
- Angewandte Chemie, Vol. 127, Issue 36
Supramolecular Chemistry in Water
journal, June 2007
- Oshovsky, Gennady V.; Reinhoudt, David N.; Verboom, Willem
- ChemInform, Vol. 38, Issue 26
Molecular Recognition of Oxoanions Based on Guanidinium Receptors
journal, May 2007
- Blondeau, Pascal; Segura, Margarita; Perez-Fernandez, Ruth
- ChemInform, Vol. 38, Issue 20
Highly Efficient Extraction of Sulfate Ions with a Tripodal Hexaurea Receptor
journal, December 2010
- Jia, Chuandong; Wu, Biao; Li, Shaoguang
- Angewandte Chemie, Vol. 123, Issue 2
Computer-Aided Design of a Sulfate-Encapsulating Receptor
journal, May 2009
- Custelcean, Radu; Bosano, Jerome; Bonnesen, Peter V.
- Angewandte Chemie, Vol. 121, Issue 22