J. Lipid Res.
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The Journal of Lipid Research, Vol. 40, 839-849, May 1999
Copyright © 1999 by Lipid Research, Inc.

Original Article

Structure and properties of totally synthetic galacto- and gluco-cerebrosides

Kumkum Saxenaa, Richard I. Duclosa, Peter Zimmermannb, Richard R. Schmidtb, and G. Graham Shipleya
a Departments of Biophysics and Biochemistry, Center for Advanced Biomedical Research, Boston University School of Medicine, 80 East Concord Street, Boston, MA 02118-2394
b Fakultat Chemie, Universitat Konstanz, D-7750 Konstanz, Germany

Correspondence to: G. Graham Shipley

The structural and thermal properties of aqueous dispersions of the totally synthetic cerebrosides, D-erythro-N-palmitoyl galactosyl- and glucosyl-C18-sphingosine (C16:0-GalCer and C16:0-GluCer, respectively) have been studied using differential scanning calorimetry (DSC) and X-ray diffraction. Over the temperature range 0–100°C, both C16:0-GalCer and C16:0-GluCer show complex thermal transitions characteristic of polymorphic behavior of exclusively bilayer phases. On heating, hydrated C16:0-GalCer undergoes an exothermic bilayer–bilayer transition at 59°C to produce a stable bilayer crystal form. X-ray diffraction at 70°C reveals a bilayer structure with an ordered hydrocarbon chain-packing arrangement. This ordered bilayer phase undergoes an endothermic chain-melting transition at 85°C to the bilayer liquid crystalline state. Similar behavior is exhibited by hydrated C16:0-GluCer which undergoes the exothermic transition at 49°C and a chain-melting transition at 87°C. The exothermic transitions observed on heating hydrated C16:0-GalCer and C16:0-GluCer are irreversible and dependent upon previous chain melting, prior cooling rate, and time of incubation at low temperatures.

Thus, the structure and properties of totally synthetic C16:0-GalCer and C16:0-GluCer with identical sphingosine (C18:1) and fatty acid (C16:0) chains are quite similar, suggesting that the precise isomeric structure of the linked sugar plays only a minor role in regulating the properties of hydrated cerebrosides. Further, these studies indicate that the complex thermal behavior and bilayer phase formation exhibited by these single-sugar cerebrosides are intrinsic properties and not due to the heterogeneity of the sphingosine base found in natural and partially synthetic cerebrosides.—Saxena, K ., R. I. Duclos, P. Zimmermann, R. R. Schmidt, and G. G. Shipley. Structure and properties of totally synthetic galacto- and gluco-cerebrosides. J. Lipid Res. 1999. 40: 839–849.

Supplementary key words: differential scanning calorimetry, X-ray diffraction, lipid bilayers, hydrocarbon chain packing, hydrogen bonding, glycolipids


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