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J. Lipid Res.
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A more recent version of this article appeared on April 1, 2005

Papers In Press, published online ahead of print January 16, 2005
J. Lipid Res., doi:10.1194/jlr.D400034-JLR200
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Submitted on November 18, 2004
Revised on December 30, 2004
Accepted on January 5, 2005

N-acylmigration in ceramides

Helena Van Overloop, Gerd Van der Hoeven, and Paul P. Van Veldhoven

Molecular Celbiology, Farmacology, Katholieke Universiteit Leuven, Leuven, Vlaams-Brabant 3000

Corresponding Author: helena.vanoverloop{at}med.kuleuven.ac.be

Upon exposure of truncated ceramides, such as N-acetyl-sphingenine, and long chain ceramides to moderate acidic conditions, three derivatives are formed. Two of them turned out to be O-acylated sphingenine, 1-O- and 3-O-acyl-sphingenine, the other was identified as sphingenine. Also truncated dihydroceramides, e.g. N-acetyl- and N-hexanoyl-sphinganine, show this type of rearrangement, which is therefore not related to the presence of the allylic hydroxy group or to the length of the N-acyl chain. Of particular concern is the fact that the O-acylated compounds, which can be considered as sphingoid base analogues, can be formed in chloroform or chloroform/methanol mixtures upon storage. For long term storage, methanol or dichloromethane are preferred solvents. A procedure to document the presence/formation of such O-acylated sphingoid bases in (dihydro)ceramide solutions in the pmol range, based on reversed phase chromatography after derivatization of their amino group with 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate, is presented.


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S. T. Pruett, A. Bushnev, K. Hagedorn, M. Adiga, C. A. Haynes, M. C. Sullards, D. C. Liotta, and A. H. Merrill Jr.
Thematic Review Series: Sphingolipids. Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols
J. Lipid Res., August 1, 2008; 49(8): 1621 - 1639.
[Abstract] [Full Text] [PDF]


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