Solution structure of diastereomeric thymidine 3′-O(N,N-diisopropyl-O-β-cyanoethylphosphoramidothioate)s by NMR spectroscopy

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Abstract

The conformational properties of a diastereomeric nucleosidephosphorothioate pair is reported as reflected by different NMR parameters. Configurational assessment is based partly on the different NOE (nuclear overhauser enhancement) effects of the individual isomers and on the trends observed in other NMR parameters. Vicinal carbon-phosphorus couplings reflect the predominance of the εt conformation for the Sp isomer and the εt conformation for the Rp isomer. The effects of solvent and temperature on these vicinal couplings are described and the results are interpreted in terms of conformational shift towards the preferred εt conformation.

Original languageEnglish
Pages (from-to)814-818
Number of pages5
JournalChirality
Volume14
Issue number10
DOIs
Publication statusPublished - 2002

Fingerprint

Isomers
Thymidine
Phosphorus
Nuclear magnetic resonance spectroscopy
Conformations
Magnetic Resonance Spectroscopy
Carbon
Temperature
Nuclear magnetic resonance

Keywords

  • C-P couplings
  • Conformational properties
  • Modified nucleotides

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

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title = "Solution structure of diastereomeric thymidine 3′-O(N,N-diisopropyl-O-β-cyanoethylphosphoramidothioate)s by NMR spectroscopy",
abstract = "The conformational properties of a diastereomeric nucleosidephosphorothioate pair is reported as reflected by different NMR parameters. Configurational assessment is based partly on the different NOE (nuclear overhauser enhancement) effects of the individual isomers and on the trends observed in other NMR parameters. Vicinal carbon-phosphorus couplings reflect the predominance of the εt conformation for the Sp isomer and the εt conformation for the Rp isomer. The effects of solvent and temperature on these vicinal couplings are described and the results are interpreted in terms of conformational shift towards the preferred εt conformation.",
keywords = "C-P couplings, Conformational properties, Modified nucleotides",
author = "E. G{\'a}cs-Baitz and M. Kajt{\'a}r-Peredy",
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T1 - Solution structure of diastereomeric thymidine 3′-O(N,N-diisopropyl-O-β-cyanoethylphosphoramidothioate)s by NMR spectroscopy

AU - Gács-Baitz, E.

AU - Kajtár-Peredy, M.

PY - 2002

Y1 - 2002

N2 - The conformational properties of a diastereomeric nucleosidephosphorothioate pair is reported as reflected by different NMR parameters. Configurational assessment is based partly on the different NOE (nuclear overhauser enhancement) effects of the individual isomers and on the trends observed in other NMR parameters. Vicinal carbon-phosphorus couplings reflect the predominance of the εt conformation for the Sp isomer and the εt conformation for the Rp isomer. The effects of solvent and temperature on these vicinal couplings are described and the results are interpreted in terms of conformational shift towards the preferred εt conformation.

AB - The conformational properties of a diastereomeric nucleosidephosphorothioate pair is reported as reflected by different NMR parameters. Configurational assessment is based partly on the different NOE (nuclear overhauser enhancement) effects of the individual isomers and on the trends observed in other NMR parameters. Vicinal carbon-phosphorus couplings reflect the predominance of the εt conformation for the Sp isomer and the εt conformation for the Rp isomer. The effects of solvent and temperature on these vicinal couplings are described and the results are interpreted in terms of conformational shift towards the preferred εt conformation.

KW - C-P couplings

KW - Conformational properties

KW - Modified nucleotides

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U2 - 10.1002/chir.10144

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SP - 814

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JF - Chirality

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