High-resolution solid-state NMR spectroscopy as a tool for investigation of enantioselective inclusion complexation

Gajda, Jarosław; Jeziorna, Agata; Ciesielski, W.; Potrzebowski, Wojciech; Prezdo, Wiktor; Potrzebowski, Marek J.

doi:10.1016/j.ssnmr.2007.04.004

Cited by 9 publications

(3 citation statements)

References 32 publications

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“…Detailed spectroscopic and thermal investigations of dehydration have been less common (but see Vogt et al11 for one extensive example). Stoichiometric solvates and inclusion complexes other than hydrates have also been the object of many studies (for example Refs 12–16…”

Section: Introductionmentioning

confidence: 99%

A Multi-Technique Approach to the Study of Structural Stability and Desolvation of Two Unusual Channel Hydrate Solvates of Finasteride

Byard

Abraham

Boulton

et al. 2012

Journal of Pharmaceutical Sciences

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Section: Introductionmentioning

confidence: 99%

A Multi-Technique Approach to the Study of Structural Stability and Desolvation of Two Unusual Channel Hydrate Solvates of Finasteride

Byard

Abraham

Boulton

et al. 2012

Journal of Pharmaceutical Sciences

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“…Many methods are currently available for computing NMR parameters. , It is known that theoretical calculations of 31 P shielding parameters, in particular for hydrogen bonded systems, are more demanding compared to the 13 C nucleus. However, as we previously showed, highly accurate data can be obtained if the proper functionals and basis sets are employed, taking into account important intermolecular interactions such as hydrogen bonding.…”

Section: Resultsmentioning

confidence: 99%

Elucidation of Structural Restraints for Phosphate Residues with Different Hydrogen Bonding and Ionization States

et al. 2008

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Solid state NMR spectroscopy and gauge including atomic orbital (GIAO) theoretical calculations were employed to establish structural restraints (ionization, hydrogen bonding, spatial arrangement) for O-phosphorylated l-threonine derivatives in different ionization states and hydrogen bonding strengths. These structural restraints are invaluable in molecular modeling and docking procedures for biological species containing phosphoryl groups. Both the experimental and the GIAO approach show that 31P delta ii chemical shift tensor parameters are very sensitive to the ionization state. The negative values found for the skew kappa are typical for -2 phosphates. The distinct span Omega values reflect the change of strength of hydrogen bonding. For species in the -1 ionization state, engaged in very strong hydrogen bonds, Omega is smaller than for a phosphate group involved in weak hydrogen bonding. For phosphates in the -2 ionization state, Omega is significantly smaller compared to -1 species, although the kappa for -1 samples never reaches negative values. For -1 phosphate residues, in the case when 1H one pulse and/or combined rotation and multiple pulse spectroscopy (CRAMPS) sequences fail and assignment of proton chemical shift is ambiguous, a combination of 1H-(13)C and 1H-(31)P 2D heteronuclear correlation (HETCOR) correlations is found to be an excellent tool for the elucidation of 1H isotropic chemical shifts. In addition, a 2D strategy using 1H-(1)H double quantum filter (DQF) correlations [a back-to-back (BABA) sequence in this work] is useful for analyzing the topology of hydrogen bonding. In the case of a multicenter phosphorus domain, 2D 31P-(31)P proton driven spin diffusion experiments give information about the spatial arrangement of the phosphate residues.

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“…Compared to liquid-state NMR spectroscopy, solid-state NMR has only found a limited number of applications for chirality studies yet. Gajda et al 44 applied 31 P solid-state NMR to study enantioselective inclusion complexation. Porto et al 45 described resin-bound chiral derivatizing agents for the assignment of molecular configuration by high-resolution MAS NMR spectroscopy.…”

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confidence: 99%

Chiral recognition in metal–organic frameworks studied by solid-state NMR spectroscopy using chiral solvating agents

et al. 2012

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High-resolution solid-state NMR spectroscopy as a tool for investigation of enantioselective inclusion complexation

Cited by 9 publications

References 32 publications

A Multi-Technique Approach to the Study of Structural Stability and Desolvation of Two Unusual Channel Hydrate Solvates of Finasteride

A Multi-Technique Approach to the Study of Structural Stability and Desolvation of Two Unusual Channel Hydrate Solvates of Finasteride

Elucidation of Structural Restraints for Phosphate Residues with Different Hydrogen Bonding and Ionization States

Chiral recognition in metal–organic frameworks studied by solid-state NMR spectroscopy using chiral solvating agents

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