Solution conformation, ion binding, and stereochemistry of griseochelin as studied by high-field nuclear magnetic resonance spectroscopy

Lajos Radics, M. Kajtár-Peredy

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Abstract

The carboxylic acid ionophore antibiotic griseochelin and its Cd 2+ salt have been studied by 13C (50 MHz), 1H (200 and 400 MHz), and 113Cd (88.73 MHz) n.m.r. spectroscopic methods. Carbon-13 spin-lattice relaxation times, H-D exchange rates of hydroxy protons, and cadmium-proton (metal-ligand) spin-spin couplings have shown that, in non-polar solvents, the essentially open-chain metabolite and its complex salt exist in a conformationally stable pseudocyclic form. This has made it possible to interpret the proton-proton couplings and nuclear Overhauser enhancement data in terms of backbone stereochemistry and to define the relative configurations at all but one of the 13 chiral centres of the molecule, rel-(2S)-2-{(2S,5S,6S; 9E,13E)-6-[(1R,2S,3S,4S,5S,6R,11R,12R)-2,4,6,12- tetrahydroxy-1,3,5,11,13,15-hexamethyloctadeca-9,13-dienyl]-5- methyltetrahydropyran-2-yl}propionic acid or its enantiomer.

Original languageEnglish
Pages (from-to)1471-1477
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number9
DOIs
Publication statusPublished - 1986

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Stereochemistry
Nuclear magnetic resonance spectroscopy
Conformations
Protons
Ions
Salts
Spin-lattice relaxation
Enantiomers
Ionophores
Metabolites
Carboxylic Acids
Cadmium
Relaxation time
Carbon
Metals
Anti-Bacterial Agents
Ligands
Molecules
zincophorin

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Solution conformation, ion binding, and stereochemistry of griseochelin as studied by high-field nuclear magnetic resonance spectroscopy",
abstract = "The carboxylic acid ionophore antibiotic griseochelin and its Cd 2+ salt have been studied by 13C (50 MHz), 1H (200 and 400 MHz), and 113Cd (88.73 MHz) n.m.r. spectroscopic methods. Carbon-13 spin-lattice relaxation times, H-D exchange rates of hydroxy protons, and cadmium-proton (metal-ligand) spin-spin couplings have shown that, in non-polar solvents, the essentially open-chain metabolite and its complex salt exist in a conformationally stable pseudocyclic form. This has made it possible to interpret the proton-proton couplings and nuclear Overhauser enhancement data in terms of backbone stereochemistry and to define the relative configurations at all but one of the 13 chiral centres of the molecule, rel-(2S)-2-{(2S,5S,6S; 9E,13E)-6-[(1R,2S,3S,4S,5S,6R,11R,12R)-2,4,6,12- tetrahydroxy-1,3,5,11,13,15-hexamethyloctadeca-9,13-dienyl]-5- methyltetrahydropyran-2-yl}propionic acid or its enantiomer.",
author = "Lajos Radics and M. Kajt{\'a}r-Peredy",
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T1 - Solution conformation, ion binding, and stereochemistry of griseochelin as studied by high-field nuclear magnetic resonance spectroscopy

AU - Radics, Lajos

AU - Kajtár-Peredy, M.

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N2 - The carboxylic acid ionophore antibiotic griseochelin and its Cd 2+ salt have been studied by 13C (50 MHz), 1H (200 and 400 MHz), and 113Cd (88.73 MHz) n.m.r. spectroscopic methods. Carbon-13 spin-lattice relaxation times, H-D exchange rates of hydroxy protons, and cadmium-proton (metal-ligand) spin-spin couplings have shown that, in non-polar solvents, the essentially open-chain metabolite and its complex salt exist in a conformationally stable pseudocyclic form. This has made it possible to interpret the proton-proton couplings and nuclear Overhauser enhancement data in terms of backbone stereochemistry and to define the relative configurations at all but one of the 13 chiral centres of the molecule, rel-(2S)-2-{(2S,5S,6S; 9E,13E)-6-[(1R,2S,3S,4S,5S,6R,11R,12R)-2,4,6,12- tetrahydroxy-1,3,5,11,13,15-hexamethyloctadeca-9,13-dienyl]-5- methyltetrahydropyran-2-yl}propionic acid or its enantiomer.

AB - The carboxylic acid ionophore antibiotic griseochelin and its Cd 2+ salt have been studied by 13C (50 MHz), 1H (200 and 400 MHz), and 113Cd (88.73 MHz) n.m.r. spectroscopic methods. Carbon-13 spin-lattice relaxation times, H-D exchange rates of hydroxy protons, and cadmium-proton (metal-ligand) spin-spin couplings have shown that, in non-polar solvents, the essentially open-chain metabolite and its complex salt exist in a conformationally stable pseudocyclic form. This has made it possible to interpret the proton-proton couplings and nuclear Overhauser enhancement data in terms of backbone stereochemistry and to define the relative configurations at all but one of the 13 chiral centres of the molecule, rel-(2S)-2-{(2S,5S,6S; 9E,13E)-6-[(1R,2S,3S,4S,5S,6R,11R,12R)-2,4,6,12- tetrahydroxy-1,3,5,11,13,15-hexamethyloctadeca-9,13-dienyl]-5- methyltetrahydropyran-2-yl}propionic acid or its enantiomer.

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