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Molecular Recognition Analyzed by Observing Intramolecular Interconversion with EPR Spectroscopy

  • Martin Jäger , Paul Schuler , Hartmut B. Stegmann and Antal Rockenbauer
Published/Copyright: June 2, 2014
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 53 Issue 12

Abstract

Molecular recognition between Rebek’s cleft R and 4-(2-benzimidazolyl)-aminomethyl-2,6-di-rm-butyl-phenol (Bi) is investigated by means of EPR spectroscopy. Their specific inter-molecular interactions are distinguished from non-specific interactions represented by mere protonation on addition of benzoic acid. Both interactions are related to intramolecular in­ terconversions at the C∞-atom of Bi*, where a two-jump mechanism is found for free and protonated Bi* and a two-site exchange for the complexed ligand. While NMR spectroscopy indicates the existence of 1:1 and 1:2 receptor-substrate complexes, the faster time scale of EPR spectroscopy allows to identify one 1 : 2 as well as three 1 : 1 associates and to elucidate their formation conditions. Based upon the corresponding hf parameters, binding modes and sites are proposed for the key-in-the-lock system.

Keywords: Rock-Key-Equilibria; Spin Labeling; Molecular Dynamics
Received: 1998-7-22
Published Online: 2014-6-2
Published in Print: 1998-12-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Die Kristallstruktur von N,N'-Ditosyl-/7-phenylendiamin, Dichtefunktionaltheorie-Berechnungen von Konformationen und Wasserstoffbrücken-Motive von Sulfonamiden / Interactions in M olecular Crystals, 146 [1, 2], The Crystal Structure of N,N'-Ditosyl-p-phenylenediam ine, Density Functional Theory Calculations of Conformations and Hydrogen Bond Motifs in Sulfonamides
  2. Wechselwirkungen in Molekülkristallen, 147 [1, 2]. Isostrukturelle Wirt/Gast-Einschluß-Verbindungen von N,N'-Ditosyl- p-phenylendiamin mit Aceton, Cyclopentanon, Cyclopent-2-en-l-on, 1,3-Dioxolan, Tetrahydrofuran und 2,5-Dihydrofuran / Interactions in Molecular Crystals, 147 [1, 2], Isostructural Host/Guest-Inclusion Compounds of N,N'-Ditosyl-p-phenylenediamine with Acetone, Cyclopentanone, Cyclopent-2-ene-l-one, 1,3-Dioxolane, Tetrahydrofurane, and 2,5-D ihydrofurane
  3. Wechselwirkungen in Molekülkristallen, 148 [1,2 ]. Wirt/Gast-Einschlußverbindungen von N,N'-Ditosyl-p-phenylendiamin mit Furan, Benzol und Dioxan / Interactions in M olecular Crystals, 148 [1, 2]. Host/Guest-Inclusion Compounds of N ,N'-Ditosyl-p-phenylenediamine with Furane, Benzene and Dioxane
  4. Wechselwirkungen in Molekülkristallen, 149 [1 -3]. Wirt/Gast-Einschlußverbindungen von NjN'-Ditosyl-p-phenylendiamin: Die Wasserstoffbrücken-Addukte mit Morpholin; Pyridin, N,N-Dimethylformamid und Dimethylsulfoxid / Interactions in Molecular Crystals, 149 [1 - 3]. Host/Guest-Inclusion Compounds of N,N'-Ditosyl-/?-phenylenediamine: The Hydrogen Bonded Adducts with Morpholine, Pyridine, N ,N -Dimethylform amide, and Dimethylsulfoxide
  5. Oligomere Tetraeder-Anionen in Borophosphaten: Sechserringe mit offenen und cyclischen Phosphat-Verzweigungen in der Kristallstruktur von K6Cu2[B4P8O28(OH)6] / Oligomeric Tetrahedral Anions in Borophosphates: Six-Membered Rings with Open and Cyclic Phosphate Branchings in the Crystal Structure of K6Cu2[B4P8O28(OH)6]
  6. Four Novel N3O4 Donor Macrocycles and their Lanthanide(III) Complexes
  7. Reaktionen des donorfreien (CF3)2Cd mit Phosphor(V)halogeniden: Difluorcarben-Einschiebungen und Direktsynthese von (CF3)3PF2 / Reactions of Donor-Free (CF3)2Cd with Phosphorus(V) Halides: Insertion of Difluorocarbene and Direct Synthesis of (CF3)3PF2
  8. Übergangsmetallkomplexe mit Schwefelliganden, CXXXIII [1]. Synthese, Struktur und Eigenschaften neuer FeII-Komplexe mit [FeN2S2]-Gerüsten / Transition Metal Complexes with Sulfur Ligands, CXXXIII [1]. Synthesis, Structure, and Properties of New FeII Complexes with [Fe2N2S2] Cores
  9. Arsenic(III), Antimony (III) and Bismuth(III) Thiobenzoates: Crystal and Molecular Structures of M(SOCR)3 and PhSb(SOCPh)2
  10. BaCu6Ge2S8 -Ein Thiogermanat als Variante der Li3Bi-Struktur / BaCu6Ge2S8 -A Thiogermanate as a Variant of the Li3Bi Structure
  11. Tetrazinn(II)-und Bariumtrizinn(II)-tetrakis[μ3 -tri-ter/-butyIsilylphosphan- diid]-Verbindungen mit einem Tetrametallatetraphosphacuban-Gerüst / Tetratin(II) and Barium Tritin(II) Tetrakis[μ3-tri-rm-butylsilylphosphandiide] Compounds with a Tetrametallatetraphosphacubane Core
  12. Determination of Coupling Signs 1J(119Sn, 15N ) and 2J(119Sn, 117Sn) in Trimethylstannylamines
  13. Metallkomplexe mit biologisch wichtigen Liganden, CIX [1]. Metallorganische Verbindungen von Platin(II), Ruthenium(II), Rhodium (III) und Iridium (III) mit Oxocarbonyl-N-geschützten a-Am inosäuren und L-Methionylglycinat / Metal Complexes with Biologically Important Ligands, CIX [1]. Organometallic Compounds of Platinum(II), Ruthenium(II), Rhodium(III), and Iridium(III) with Oxocarbonyl-N-protected a-Amino Acids and L-Methionylglycinate
  14. Phosphenium-Komplexe, XXIX [1]. [4+2]-Cycloadditionen von Phospheniumkomplexen des Typs Cp(OC)2W = PR2(R = Alkyl, Aryl) mit 2,3-Dimethylbutadien / Phosphenium Complexes, XXIX [1], [4+2]-Cycloaddition of Phosphenium Complexes of the Type Cp(OC)2W=PR2 (R = Alkyl, Aryl) with 2,3-Dimethylbutadiene
  15. Molecular Recognition Analyzed by Observing Intramolecular Interconversion with EPR Spectroscopy
  16. Synthesis of the Stereoisomers of β-Hydroxyhistidine and their Analytical Identification in Hydrolysates of Bacterial Peptides
  17. The Structure of Lithiumiodide 3-Tetrahydrofuran
  18. Benzo-18-krone-6 -Acetonitril (1/2): Kristallisation und Tieftemperatur- Röntgenstrukturanalyse / Benzo-18 -crown-6 -Acetonitrile (1/2): Crystallization and Low-Temperature X-Ray Analysis
  19. Subject Index
  20. Authors Index
https://doi.org/10.1515/znb-1998-1215
Keywords for this article
Rock-Key-Equilibria; Spin Labeling; Molecular Dynamics

Articles in the same Issue

  1. Die Kristallstruktur von N,N'-Ditosyl-/7-phenylendiamin, Dichtefunktionaltheorie-Berechnungen von Konformationen und Wasserstoffbrücken-Motive von Sulfonamiden / Interactions in M olecular Crystals, 146 [1, 2], The Crystal Structure of N,N'-Ditosyl-p-phenylenediam ine, Density Functional Theory Calculations of Conformations and Hydrogen Bond Motifs in Sulfonamides
  2. Wechselwirkungen in Molekülkristallen, 147 [1, 2]. Isostrukturelle Wirt/Gast-Einschluß-Verbindungen von N,N'-Ditosyl- p-phenylendiamin mit Aceton, Cyclopentanon, Cyclopent-2-en-l-on, 1,3-Dioxolan, Tetrahydrofuran und 2,5-Dihydrofuran / Interactions in Molecular Crystals, 147 [1, 2], Isostructural Host/Guest-Inclusion Compounds of N,N'-Ditosyl-p-phenylenediamine with Acetone, Cyclopentanone, Cyclopent-2-ene-l-one, 1,3-Dioxolane, Tetrahydrofurane, and 2,5-D ihydrofurane
  3. Wechselwirkungen in Molekülkristallen, 148 [1,2 ]. Wirt/Gast-Einschlußverbindungen von N,N'-Ditosyl-p-phenylendiamin mit Furan, Benzol und Dioxan / Interactions in M olecular Crystals, 148 [1, 2]. Host/Guest-Inclusion Compounds of N ,N'-Ditosyl-p-phenylenediamine with Furane, Benzene and Dioxane
  4. Wechselwirkungen in Molekülkristallen, 149 [1 -3]. Wirt/Gast-Einschlußverbindungen von NjN'-Ditosyl-p-phenylendiamin: Die Wasserstoffbrücken-Addukte mit Morpholin; Pyridin, N,N-Dimethylformamid und Dimethylsulfoxid / Interactions in Molecular Crystals, 149 [1 - 3]. Host/Guest-Inclusion Compounds of N,N'-Ditosyl-/?-phenylenediamine: The Hydrogen Bonded Adducts with Morpholine, Pyridine, N ,N -Dimethylform amide, and Dimethylsulfoxide
  5. Oligomere Tetraeder-Anionen in Borophosphaten: Sechserringe mit offenen und cyclischen Phosphat-Verzweigungen in der Kristallstruktur von K6Cu2[B4P8O28(OH)6] / Oligomeric Tetrahedral Anions in Borophosphates: Six-Membered Rings with Open and Cyclic Phosphate Branchings in the Crystal Structure of K6Cu2[B4P8O28(OH)6]
  6. Four Novel N3O4 Donor Macrocycles and their Lanthanide(III) Complexes
  7. Reaktionen des donorfreien (CF3)2Cd mit Phosphor(V)halogeniden: Difluorcarben-Einschiebungen und Direktsynthese von (CF3)3PF2 / Reactions of Donor-Free (CF3)2Cd with Phosphorus(V) Halides: Insertion of Difluorocarbene and Direct Synthesis of (CF3)3PF2
  8. Übergangsmetallkomplexe mit Schwefelliganden, CXXXIII [1]. Synthese, Struktur und Eigenschaften neuer FeII-Komplexe mit [FeN2S2]-Gerüsten / Transition Metal Complexes with Sulfur Ligands, CXXXIII [1]. Synthesis, Structure, and Properties of New FeII Complexes with [Fe2N2S2] Cores
  9. Arsenic(III), Antimony (III) and Bismuth(III) Thiobenzoates: Crystal and Molecular Structures of M(SOCR)3 and PhSb(SOCPh)2
  10. BaCu6Ge2S8 -Ein Thiogermanat als Variante der Li3Bi-Struktur / BaCu6Ge2S8 -A Thiogermanate as a Variant of the Li3Bi Structure
  11. Tetrazinn(II)-und Bariumtrizinn(II)-tetrakis[μ3 -tri-ter/-butyIsilylphosphan- diid]-Verbindungen mit einem Tetrametallatetraphosphacuban-Gerüst / Tetratin(II) and Barium Tritin(II) Tetrakis[μ3-tri-rm-butylsilylphosphandiide] Compounds with a Tetrametallatetraphosphacubane Core
  12. Determination of Coupling Signs 1J(119Sn, 15N ) and 2J(119Sn, 117Sn) in Trimethylstannylamines
  13. Metallkomplexe mit biologisch wichtigen Liganden, CIX [1]. Metallorganische Verbindungen von Platin(II), Ruthenium(II), Rhodium (III) und Iridium (III) mit Oxocarbonyl-N-geschützten a-Am inosäuren und L-Methionylglycinat / Metal Complexes with Biologically Important Ligands, CIX [1]. Organometallic Compounds of Platinum(II), Ruthenium(II), Rhodium(III), and Iridium(III) with Oxocarbonyl-N-protected a-Amino Acids and L-Methionylglycinate
  14. Phosphenium-Komplexe, XXIX [1]. [4+2]-Cycloadditionen von Phospheniumkomplexen des Typs Cp(OC)2W = PR2(R = Alkyl, Aryl) mit 2,3-Dimethylbutadien / Phosphenium Complexes, XXIX [1], [4+2]-Cycloaddition of Phosphenium Complexes of the Type Cp(OC)2W=PR2 (R = Alkyl, Aryl) with 2,3-Dimethylbutadiene
  15. Molecular Recognition Analyzed by Observing Intramolecular Interconversion with EPR Spectroscopy
  16. Synthesis of the Stereoisomers of β-Hydroxyhistidine and their Analytical Identification in Hydrolysates of Bacterial Peptides
  17. The Structure of Lithiumiodide 3-Tetrahydrofuran
  18. Benzo-18-krone-6 -Acetonitril (1/2): Kristallisation und Tieftemperatur- Röntgenstrukturanalyse / Benzo-18 -crown-6 -Acetonitrile (1/2): Crystallization and Low-Temperature X-Ray Analysis
  19. Subject Index
  20. Authors Index
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