Journal of Lipid Research, Vol 33, 1227-1232, Copyright © 1992 by Lipid Research, Inc.

ARTICLES

Galactosylceramide containing omega-amino-fatty acids: preparation, characterization, and sulfotransferase acceptor

K Kamio, S Gasa and A Makita
Biochemistry Laboratory, Hokkaido University School of Medicine, Sapporo, Japan.

For preparation of an affinity ligand, an N-fatty acyl moiety of galactosylceramide (GalCer) was chemically replaced with omega-amino- fatty acid including amino-n-hexanoic acid or amino-n-dodecanoic acid to obtain omega-aminoGalCer. For the synthesis of the compound, galactosylsphingosine (GalSph) was coupled with N-trifluoroacetyl omega- amino-fatty acid which was prepared by a reaction with S- ethyltrifluorothioacetate. After removal of the N-trifluoroacetyl group in a mild alkaline solution, in which an N-fatty acyl group was retained, aminoGalCer composed of an N-hexanoyl or an N-dodecanoyl group was obtained with an overall yield of 90%. Their chemical structures were confirmed by proton nuclear magnetic resonance and fast atom bombardment-mass spectrometries. These aminoGalCers and GalSph as well as immobilized aminoGalCer were sulfated by a glycolipid sulfotransferase from rat kidney. Furthermore, immobilized aminoGalCer on gel matrix was used for affinity chromatography of the sulfotransferase, resulting in an excellent increase in the purification (14,000-fold) with a recovery rate of 40%.
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