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Journal of Lipid Research, Vol. 12, 760-765, November 1971
Copyright © 1971 by Lipid Research, Inc.

A convenient procedure for the synthesis of ceramides

Sven Hammarström

Department of Medical Chemistry, Royal Veterinary College, Stockholm 50, Sweden

A procedure for the preparation of ceramides by direct coupling of long-chain bases and fatty acids in the presence of a mixed carbodiimide is described. This method has been used to prepare ceramides containing sphing-4-enine or sphinganine and various saturated and unsaturated fatty acids as well as saturated 2-hydroxy acids. Ceramides containing 4-hydroxy sphinganine and saturated nonhydroxy acids have also been prepared. The yields were 60-75%. The characterization of these compounds by gas-liquid chromatography-mass spectrometry as trimethylsilyl derivatives has been previously reported. Some of the ceramides are further characterized in this report by infrared spectroscopy and one compound, in addition, by elementary analysis. Use of racemic constituents for 2-hydroxy acid ceramide syntheses leads to the formation of diastereoisomers which separate by thin-layer chromatography. These were characterized by gas-liquid chromatography-mass spectrometry as the trimethylsilyl derivatives and by infrared spectroscopy. Their configurations were established by syntheses with optically active constituents.

Supplementary key words sphing-4-enine • sphinganine • 4-hydroxy sphinganine • saturated and unsaturated fatty acids • 2-hydroxy acids • infrared spectroscopy • diastereoisomerism • thin-layer chromatography

Submitted on April 7, 1971
Accepted on July 6, 1971


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