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Macrocycle Conformation and Self-Inclusion Phenomena in octakis(3-O-butanoyl-2,6-di-O-pentyl)-gamma-cyclodextrin (Lipodex E) by NMR Spectroscopy and Molecular Dynamics

Macrocycle Conformation and Self-Inclusion Phenomena in octakis(3-O-butanoyl-2,6-di-O-pentyl)-gamma-cyclodextrin (Lipodex E) by NMR Spectroscopy and Molecular Dynamics

Andrea Mele, Giuseppina Raffaini, Fabio Ganazzoli, Markus Juza, Volker Schurig

Carbohydr Res. 2003 Mar 28;338(7):625-35.

PMID: 12644376

Abstract:

Octakis(3-O-butanoyl-2,6-di-O-pentyl)-gamma-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, 3J(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 gammaCD.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS7413147	Octakis (2,6-di-O-pentyl)-γ-cyclodextrin			Price

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