Cations George W Gokel abc and Joseph W Meisel ab a Center for Nanoscience b Department of Chemistry and Biochemistry c Department of Biology University of MissouriSt Louis 1 University Blvd ID: 643258
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Chapter 3. Synthetic Receptors for Alkali Metal Cations
George W. Gokel*a,b,c and Joseph W. Meisela,baCenter for Nanoscience, bDepartment of Chemistry and Biochemistry, cDepartment of Biology, University of Missouri-St. Louis, 1 University Blvd. Saint Louis, MO 63121 USA *Email: gokelg@umsl.edu
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Chart 3.1
Solid state structure of the polyether ionophore, monensin A, binding Na+.
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Chart 3.2
Partial structures of two biological ion channels showing: (A) Two Na+ binding sites in the LeuT Na+-dependent pump (PDB code 2A65). (B) Four K+ binding sites in the KcsA K+ channel (PDB code 1K4C). (Reproduced with permission from Science 2005, 310, 1461, © American Association for the Advancement of
Science)
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Figure 3.1
Coordination compounds and bidentate complexes
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Figure 3.2
The chemistry leading to the first crown ethers.
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Figure 3.3
Solid state structure of dibenzo-18-crown-6 binding K+ (CSD: BEBFAP).
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Figure 3.4
Two-armed diaza-18-crown-6 derivatives having three atom sidearms.
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Table 3.1
Homogeneous complexation constants and thermodynamic parameters determined in methanola,b.
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Figure 3.5
Binding constants determined in 100% methanol solution for 3n-crown-n compounds where n = 4 – 8.
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Figure 3.6
Solid state structures of uncomplexed 12-crown-4 (CSD: TOXCDP) and K+ ion complexed by 18-crown-6 (CSD: KTHOXD).
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Figure 3.7
Solid state structures of (12C4)2•Na+ (CSD: BEYHES) and ( Aza-12C4)2•Na+ (CSD: FEHDOL).
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Figure 3.8
Solvent dependence of 18-crown-6•Na+ binding in methanol and water.
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Figure 3.9
Structures of [2.1.1]cryptand and [3.2.2]cryptand.
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Figure 3.10
Solid state structure of [2.2.2]cryptand complexing KI.
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Figure 3.11
Left: a spherand. Center: a hemispherand. Right a crown-hemispherand.
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Figure 3.12
Macrocyclic compounds formed by acid-catalyzed, multiple condensations. Supplementary information for Synthetic Receptors for Biomolecules: Design Principles and Applications©
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Figure 3.13
Calixarene receptor molecules.
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Figure 3.14
K+ complexation by a calix-crown.
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Figure
3.15 Comparison of homogeneous binding and extractions constants with transport rate.
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Figure
3.16 Schematic representation of a liposome and a typical phospholipid.
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Figure
3.17 Redox-switched molecular receptors. Supplementary information for
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Figure
3.18 Examples of host molecules that can be photo-switched.
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Figure
3.19 Relative NH4+ binding strengths for 18-membered ring macrocycles.
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Figure
3.20 Crown ether-derived colorimetric sensors: “chromoionophores”.
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Figure
3.21 Fluoroionophores based on crown ethers and calixarenes.
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Figure
3.22 Chemical structure of the cyclic peptide K+ carrier valinomycin.
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Figure
3.23 (Top) Single-armed carbon-pivot and nitrogen pivot lariat ethers. (Bottom) a two-armed or bibracchial nitrogen-pivot lariat ether.
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Figure
3.24 Solid state structure of 4,13-diaza-18-crown-6 having two methoxyethyl side arms attached to nitrogen and binding KI.
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Table
2 Sodium and potassium cation binding by lariat ethers expressed as log10 KS.
a
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Figure
3.25 Bibracchial lariat ethers containing π-donor side arms. Supplementary information for Synthetic Receptors for Biomolecules: Design Principles and Applications
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Figure
3.26 Solid state structures of phenyl (CSD: OCABEZ) and pentafluorobenzyl (CSD: OCACIE) side-armed bibracchial lariat ethers binding KI.
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Figure
3.27 Solid state structure of a calixarene•2Cs+ complex (CSD: RADBUT).
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Figure
3.28 A ditopic receptor binding both Na+ and I- (CSD: IBUKUM).
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Figure
3.29 An ion-conducting channel based on the cyclodextrin scaffold.
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Figure
3.30 Channel designs reported by Lehn (left) and by Fyles and their coworkers.
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Figure
3.31 The hydraphile channel concept.
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Figure
3.32 An array of synthetic amphiphiles that show channel-like function.
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