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J. Lipid Res.
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Originally published In Press as doi:10.1194/jlr.D400034-JLR200 on January 16, 2005

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Journal of Lipid Research, Vol. 46, 812-816, April 2005
Copyright © 2005 by American Society for Biochemistry and Molecular Biology

Methods

N-Acyl migration in ceramides

Helena Van Overloop, Gerd Van der Hoeven and Paul P. Van Veldhoven1

Katholieke Universiteit Leuven, Faculteit Geneeskunde, Departement Moleculaire Celbiologie, Afdeling Farmacologie, Leuven, Belgium

1 To whom correspondence should be addressed. e-mail: paul.vanveldhoven{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, and the other was identified as sphingenine. Truncated dihydroceramides (e.g., N-acetyl- and N-hexanoyl-sphinganine) also 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 sphingoid base analogs, can be formed in chloroform or chloroform-methanol mixtures upon storage. For long-term storage, methanol or dichloromethane is the preferred solvent.

A procedure to document the presence/formation of such O-acylated sphingoid bases in ceramide solutions in the picomole range, based on reversed-phase chromatography after derivatization of their amino group with 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate, is presented.

Supplementary key words O-acylation • N-acylethanolamine • anandamide • hydroxyoxazolidine • ceramide kinase


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