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Title: Siderophore-inspired chelator hijacks uranium from aqueous medium

Abstract

Over millennia, nature has evolved an ability to selectively recognize and sequester specific metal ions by employing a wide variety of supramolecular chelators. Iron-specific molecular carriers—siderophores—are noteworthy for their structural elegance, while exhibiting some of the strongest and most selective binding towards a specific metal ion. Development of simple uranyl (UO22+) recognition motifs possessing siderophore-like selectivity, however, presents a challenge. Herein we report a comprehensive theoretical, crystallographic and spectroscopic studies on the UO22+ binding with a non-toxic siderophore-inspired chelator, 2,6-bis[hydroxy(methyl)amino]-4-morpholino-1,3,5-triazine (H2BHT). The optimal pKa values and structural preorganization endow H2BHT with one of the highest uranyl binding affinity and selectivity among molecular chelators. The results of small-molecule standards are validated by a proof-of-principle development of the H2BHT-functionalized polymeric adsorbent material that affords high uranium uptake capacity even in the presence of competing vanadium (V) ions in aqueous medium.

Authors:
ORCiD logo [1]; ORCiD logo [2];  [3]; ORCiD logo [4];  [4]; ORCiD logo [4];  [1];  [2];  [1]; ORCiD logo [1]; ORCiD logo [1];  [3]; ORCiD logo [1]
  1. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
  2. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Univ. of California, Berkeley, CA (United States)
  3. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
  4. Univ. of South Florida, Tampa, FL (United States)
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Nuclear Energy (NE); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Chemical Sciences, Geosciences & Biosciences Division
OSTI Identifier:
1495975
Alternate Identifier(s):
OSTI ID: 1559186
Grant/Contract Number:  
AC05-00OR22725; AC02-05CH11231; NE0008281
Resource Type:
Accepted Manuscript
Journal Name:
Nature Communications
Additional Journal Information:
Journal Volume: 10; 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

Ivanov, Alexander S., Parker, Bernard F., Zhang, Zhicheng, Aguila, Briana, Sun, Qi, Ma, Shengqian, Jansone-Popova, Santa, Arnold, John, Mayes, Richard T., Dai, Sheng, Bryantsev, Vyacheslav S., Rao, Linfeng, and Popovs, Ilja. Siderophore-inspired chelator hijacks uranium from aqueous medium. United States: N. p., 2019. Web. doi:10.1038/s41467-019-08758-1.
Ivanov, Alexander S., Parker, Bernard F., Zhang, Zhicheng, Aguila, Briana, Sun, Qi, Ma, Shengqian, Jansone-Popova, Santa, Arnold, John, Mayes, Richard T., Dai, Sheng, Bryantsev, Vyacheslav S., Rao, Linfeng, & Popovs, Ilja. Siderophore-inspired chelator hijacks uranium from aqueous medium. United States. doi:10.1038/s41467-019-08758-1.
Ivanov, Alexander S., Parker, Bernard F., Zhang, Zhicheng, Aguila, Briana, Sun, Qi, Ma, Shengqian, Jansone-Popova, Santa, Arnold, John, Mayes, Richard T., Dai, Sheng, Bryantsev, Vyacheslav S., Rao, Linfeng, and Popovs, Ilja. Mon . "Siderophore-inspired chelator hijacks uranium from aqueous medium". United States. doi:10.1038/s41467-019-08758-1. https://www.osti.gov/servlets/purl/1495975.
@article{osti_1495975,
title = {Siderophore-inspired chelator hijacks uranium from aqueous medium},
author = {Ivanov, Alexander S. and Parker, Bernard F. and Zhang, Zhicheng and Aguila, Briana and Sun, Qi and Ma, Shengqian and Jansone-Popova, Santa and Arnold, John and Mayes, Richard T. and Dai, Sheng and Bryantsev, Vyacheslav S. and Rao, Linfeng and Popovs, Ilja},
abstractNote = {Over millennia, nature has evolved an ability to selectively recognize and sequester specific metal ions by employing a wide variety of supramolecular chelators. Iron-specific molecular carriers—siderophores—are noteworthy for their structural elegance, while exhibiting some of the strongest and most selective binding towards a specific metal ion. Development of simple uranyl (UO22+) recognition motifs possessing siderophore-like selectivity, however, presents a challenge. Herein we report a comprehensive theoretical, crystallographic and spectroscopic studies on the UO22+ binding with a non-toxic siderophore-inspired chelator, 2,6-bis[hydroxy(methyl)amino]-4-morpholino-1,3,5-triazine (H2BHT). The optimal pKa values and structural preorganization endow H2BHT with one of the highest uranyl binding affinity and selectivity among molecular chelators. The results of small-molecule standards are validated by a proof-of-principle development of the H2BHT-functionalized polymeric adsorbent material that affords high uranium uptake capacity even in the presence of competing vanadium (V) ions in aqueous medium.},
doi = {10.1038/s41467-019-08758-1},
journal = {Nature Communications},
number = 1,
volume = 10,
place = {United States},
year = {2019},
month = {2}
}

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Cited by: 11 works
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Figures / Tables:

Fig. 1 Fig. 1: Structures of ligands for selective recognition of metal ions. a Glutaroimide-dioxime (H3IDO) ligand, which is the major functional unit of polyamidoxime adsorbents for uranium recovery from seawater. b Cartoon representation of the ferric hydroxamate uptake (FhuA) protein (image from the RCSB PDB (www.rcsb.org) of PDB ID 1BY5) withmore » the highlighted structure of ferrichrome—a natural siderophore. c Bis-(hydroxylamino)-1,3,5-triazine (H2BHT)—an artificial siderophore investigated in this study« less

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Works referenced in this record:

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    Works referencing / citing this record:

    Solid-Supported Chloro[1,3,5]triazine. A Versatile New Synthetic Auxiliary for the Synthesis of Amide Libraries
    journal, November 1999

    • Masala, Simonetta; Taddei, Maurizio
    • Organic Letters, Vol. 1, Issue 9
    • DOI: 10.1021/ol990215h

    First-Principles Integrated Adsorption Modeling for Selective Capture of Uranium from Seawater by Polyamidoxime Sorbent Materials
    journal, December 2017

    • Ladshaw, Austin P.; Ivanov, Alexander S.; Das, Sadananda
    • ACS Applied Materials & Interfaces, Vol. 10, Issue 15
    • DOI: 10.1021/acsami.7b17031

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    Investigations into the Reusability of Amidoxime-Based Polymeric Adsorbents for Seawater Uranium Extraction
    journal, September 2017

    • Kuo, Li-Jung; Pan, Horng-Bin; Wai, Chien M.
    • Industrial & Engineering Chemistry Research, Vol. 56, Issue 40
    • DOI: 10.1021/acs.iecr.7b02893

    A Comparative IRMPD and DFT Study of Fe 3+ and UO 2 2+ Complexation with N -Methylacetohydroxamic Acid
    journal, January 2018


    A Hybrid Macrocycle with a Pyridine Subunit Displays Aromatic Character upon Uranyl Cation Complexation
    journal, March 2014

    • Ho, I-Ting; Zhang, Zhan; Ishida, Masatoshi
    • Journal of the American Chemical Society, Vol. 136, Issue 11
    • DOI: 10.1021/ja412520g

    A protein engineered to bind uranyl selectively and with femtomolar affinity
    journal, January 2014

    • Zhou, Lu; Bosscher, Mike; Zhang, Changsheng
    • Nature Chemistry, Vol. 6, Issue 3
    • DOI: 10.1038/nchem.1856

    Complexation of uranium (VI) with the siderophore desferrioxamine B
    journal, June 2007

    • Mullen, L.; Gong, C.; Czerwinski, K.
    • Journal of Radioanalytical and Nuclear Chemistry, Vol. 273, Issue 3
    • DOI: 10.1007/s10967-007-0931-5

    Materials for the Recovery of Uranium from Seawater
    journal, June 2017


    Naphthylbipyrrole-Containing Amethyrin Analogue: A New Ligand for the Uranyl (UO 2 2+ ) Cation
    journal, July 2017


    Mining Critical Metals and Elements from Seawater: Opportunities and Challenges
    journal, April 2015

    • Diallo, Mamadou S.; Kotte, Madhusudhana Rao; Cho, Manki
    • Environmental Science & Technology, Vol. 49, Issue 16
    • DOI: 10.1021/acs.est.5b00463

    Selective recognition and extraction of the uranyl ion from aqueous solutions with a recyclable chelating resin
    journal, January 2013

    • Sather, Aaron C.; Berryman, Orion B.; Rebek, Julius
    • Chemical Science, Vol. 4, Issue 9
    • DOI: 10.1039/c3sc51507a

    Efficient Functionalization of Polyethylene Fibers for the Uranium Extraction from Seawater through Atom Transfer Radical Polymerization
    journal, September 2017

    • Neti, Venkata S.; Das, Sadananda; Brown, Suree
    • Industrial & Engineering Chemistry Research, Vol. 56, Issue 38
    • DOI: 10.1021/acs.iecr.7b00482

    Novel poly(imide dioxime) sorbents: Development and testing for enhanced extraction of uranium from natural seawater
    journal, August 2016


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    journal, January 2009


    Ultrafast and Highly Selective Uranium Extraction from Seawater by Hydrogel-like Spidroin-based Protein Fiber
    journal, July 2019

    • Yuan, Yihui; Yu, Qiuhan; Wen, Jun
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    journal, November 2015

    • Hu, Jiangtao; Ma, Hongjuan; Xing, Zhe
    • Industrial & Engineering Chemistry Research, Vol. 55, Issue 15
    • DOI: 10.1021/acs.iecr.5b03175

    Origin of the unusually strong and selective binding of vanadium by polyamidoximes in seawater
    journal, November 2017

    • Ivanov, Alexander S.; Leggett, Christina J.; Parker, Bernard F.
    • Nature Communications, Vol. 8, Issue 1
    • DOI: 10.1038/s41467-017-01443-1

    Extracting Minerals from Seawater: An Energy Analysis
    journal, April 2010


    A Facile Synthesis of Poly(acrylanilide-co-acrylic Acid)
    journal, January 2013


    Tris-(hydroxyamino)triazines: high-affinity chelating tridentate O,N,O-hydroxylamine ligand for the cis-VVO2+ cation
    journal, January 2010

    • Nikolakis, Vladimiros A.; Exarchou, Vassiliki; Jakusch, Tamás
    • Dalton Transactions, Vol. 39, Issue 38
    • DOI: 10.1039/c0dt00574f

    Selective Recognition and Extraction of the Uranyl Ion
    journal, October 2010

    • Sather, Aaron C.; Berryman, Orion B.; Rebek, Julius
    • Journal of the American Chemical Society, Vol. 132, Issue 39
    • DOI: 10.1021/ja1035607

    Ultrafast and Highly Selective Uranium Extraction from Seawater by Hydrogel‐like Spidroin‐based Protein Fiber
    journal, July 2019


    A Peptoid-Based Combinatorial and Computational Approach to Developing Ligands for Uranyl Sequestration from Seawater
    journal, December 2015

    • Parker, Bernard F.; Knight, Abigail S.; Vukovic, Sinisa
    • Industrial & Engineering Chemistry Research, Vol. 55, Issue 15
    • DOI: 10.1021/acs.iecr.5b03500

    Complexation of glutarimidedioxime with Fe(iii), Cu(ii), Pb(ii), and Ni(ii), the competing ions for the sequestration of U(vi) from seawater
    journal, January 2013

    • Sun, Xiaoqi; Xu, Chao; Tian, Guoxin
    • Dalton Transactions, Vol. 42, Issue 40
    • DOI: 10.1039/c3dt51767e

    Elution of Uranium and Transition Metals from Amidoxime-Based Polymer Adsorbents for Sequestering Uranium from Seawater
    journal, December 2015

    • Pan, Horng-Bin; Kuo, Li-Jung; Wai, Chien M.
    • Industrial & Engineering Chemistry Research, Vol. 55, Issue 15
    • DOI: 10.1021/acs.iecr.5b03307

    Uranium Adsorbent Fibers Prepared by Atom-Transfer Radical Polymerization from Chlorinated Polypropylene and Polyethylene Trunk Fibers
    journal, December 2015

    • Brown, Suree; Chatterjee, Sabornie; Li, Meijun
    • Industrial & Engineering Chemistry Research, Vol. 55, Issue 15
    • DOI: 10.1021/acs.iecr.5b03667

    Seven chemical separations to change the world
    journal, April 2016

    • Sholl, David S.; Lively, Ryan P.
    • Nature, Vol. 532, Issue 7600
    • DOI: 10.1038/532435a

    A half-wave rectified alternating current electrochemical method for uranium extraction from seawater
    journal, February 2017


    Bis(hydroxylamino)triazines: High Selectivity and Hydrolytic Stability of Hydroxylamine-Based Ligands for Uranyl Compared to Vanadium(V) and Iron(III)
    journal, June 2018


    Bio-inspired nano-traps for uranium extraction from seawater and recovery from nuclear waste
    journal, April 2018


    Hexadentate Terephthalamide(bis-hydroxypyridinone) Ligands for Uranyl Chelation: Structural and Thermodynamic Consequences of Ligand Variation(1)
    journal, May 2011

    • Szigethy, Géza; Raymond, Kenneth N.
    • Journal of the American Chemical Society, Vol. 133, Issue 20
    • DOI: 10.1021/ja201511u

    Uranium Adsorbent Fibers Prepared by Atom-Transfer Radical Polymerization (ATRP) from Poly(vinyl chloride)- co -chlorinated Poly(vinyl chloride) (PVC- co -CPVC) Fiber
    journal, December 2015

    • Brown, Suree; Yue, Yanfeng; Kuo, Li-Jung
    • Industrial & Engineering Chemistry Research, Vol. 55, Issue 15
    • DOI: 10.1021/acs.iecr.5b03355

    Efficient Removal and Recovery of Uranium by a Layered Organic–Inorganic Hybrid Thiostannate
    journal, September 2016

    • Feng, Mei-Ling; Sarma, Debajit; Qi, Xing-Hui
    • Journal of the American Chemical Society, Vol. 138, Issue 38
    • DOI: 10.1021/jacs.6b07351

    Siderophore Mediated Plutonium Accumulation by Microbacterium flavescens (JG-9)
    journal, July 2001

    • John, Seth G.; Ruggiero, Christy E.; Hersman, Larry E.
    • Environmental Science & Technology, Vol. 35, Issue 14
    • DOI: 10.1021/es010590g

    Uranylpentaphyrin: an actinide complex of an expanded porphyrin
    journal, June 1991

    • Burrell, Anthony K.; Hemmi, Gregory; Lynch, Vincent
    • Journal of the American Chemical Society, Vol. 113, Issue 12
    • DOI: 10.1021/ja00012a053

    Adsorption of Uranium(VI) to Manganese Oxides: X-ray Absorption Spectroscopy and Surface Complexation Modeling
    journal, December 2012

    • Wang, Zimeng; Lee, Sung-Woo; Catalano, Jeffrey G.
    • Environmental Science & Technology, Vol. 47, Issue 2
    • DOI: 10.1021/es304454g

    Ultrafast and Highly Selective Uranium Extraction from Seawater by Hydrogel‐like Spidroin‐based Protein Fiber
    journal, July 2019


    Ultrafast and Highly Selective Uranium Extraction from Seawater by Hydrogel-like Spidroin-based Protein Fiber
    journal, July 2019

    • Yuan, Yihui; Yu, Qiuhan; Wen, Jun
    • Angewandte Chemie International Edition, Vol. 58, Issue 34
    • DOI: 10.1002/anie.201906191

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