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Conformation of the polar headgroup of sphingomyelin and its analogues

Authors
Journal
Biochimica et Biophysica Acta (BBA) - Biomembranes
0005-2736
Publisher
Elsevier
Publication Date
Volume
939
Issue
2
Identifiers
DOI: 10.1016/0005-2736(88)90076-4
Keywords
  • Sphingomyelin
  • Headgroup Conformation
  • Phospholipid Bilayer
Disciplines
  • Chemistry

Abstract

Abstract The conformation of the polar headgroup of synthetic d- erythro-stearoylsphingomyelin (1), its l- threo-isomer (2) and phosphorothioyl analogues of 1 (3 and 4) has been studied in detail by high-resolution NMR spectroscopy. In both monomeric and aggregated states the phosphocholine function of 1 adopts the synclinal conformation (α 5 torsional angle), in analogy with phosphatidylcholine (Hauser, H., Guyer, W., Pascher, I ., Skrabal, P. and Sundell, S. (1980) Biochemistry 19, 366–373). The conformation about the C1C2 bond (θ 1 angle) of the sphingosine backbone is predominantly —synclinal, analogously to the conformation of the crystalline galactosyl cerebroside (Pascher, I. and Sundell, S. (1977) Chem. Phys. Lipids 20, 175–191). In contrast, the l- threo-isomer displays unrestricted rotation about C1C2 bond. The possibility of the existence of a hydrogen bond between the 3-hydroxyl function and the bridged oxygen atom of sphingosine responsible for the different conformation of 1 and 2 is discussed. The modification of the phosphate function in 1 with sulfur has no significant effect on the conformation of the resulting analogues. The conformation of all studied compounds about the CO phosphoester bonds (α 1 and α 4 torsion angles) is mainly antiperiplanar. Similar to other double-chain phospholipids, sphingomyelin shows a preference towards the antiperiplanar conformation about the C2C3 bond.

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