Macrocycle conformation and self-inclusion phenomena in octakis(3- O-butanoyl-2,6-di- O-pentyl)-γ-cyclodextrin (Lipodex E) by NMR spectroscopy and molecular dynamics

Octakis(3- O-butanoyl-2,6-di- O-pentyl)-γ-cyclodextrin (Lipodex E) is a lipophilic chiral selector successfully used for the enantioselective gas chromatographic separation of a multitude of racemic analytes. NMR data ( 13C chemical shifts, 3 J HH, rotating frame NOEs (ROEs)) and molecular dynamics...

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Bibliographic Details
Published in:Carbohydrate research 2003-03, Vol.338 (7), p.625-635
Main Authors: Mele, Andrea, Raffaini, Giuseppina, Ganazzoli, Fabio, Juza, Markus, Schurig, Volker
Format: Article
Language:English
Subjects:
Computer Simulation
Cyclodextrins
Cyclodextrins - chemistry
gamma-Cyclodextrins
Lipodex E
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Conformation
Molecular dynamics
Molecular Structure
NMR spectroscopy
Nuclear Overhauser effect
Radial distribution function
Time Factors
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Summary:Octakis(3- O-butanoyl-2,6-di- O-pentyl)-γ-cyclodextrin (Lipodex E) is a lipophilic chiral selector successfully used for the enantioselective gas chromatographic separation of a multitude of racemic analytes. NMR data ( 13C chemical shifts, 3 J HH, rotating frame NOEs (ROEs)) and molecular dynamics (MD) simulations point out that the macrocycle is distorted with respect to the canonical truncated-cone shape of native cyclodextrins, although C 8 symmetry is retained on the NMR timescale. ROE data and MD trajectories provide evidence for self-inclusion of one 6- O-pentyl pendant chain within the cavity of Lipodex E. The interpretation of long-range and low-intensity ROEs is supported by the calculation of average internuclear distances by using the radial distribution function (RDF) calculated from MD trajectories. MD simulations are eventually used to compare the flexibility of the macrocycle of Lipodex E with that of native γCD. Graphic
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(02)00493-7