Galactosylceramide containing omega-amino-fatty acids: preparation, characterization, and sulfotransferase acceptor.
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) w...
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1992-08-01
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doaj-455a021126684a09b3b82d818d65af492021-04-26T05:51:34ZengElsevierJournal of Lipid Research0022-22751992-08-0133812271232Galactosylceramide containing omega-amino-fatty acids: preparation, characterization, and sulfotransferase acceptor.K Kamio0S Gasa1A Makita2Biochemistry Laboratory, Hokkaido University School of Medicine, Sapporo, Japan.Biochemistry Laboratory, Hokkaido University School of Medicine, Sapporo, Japan.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%.http://www.sciencedirect.com/science/article/pii/S0022227520407758 |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
K Kamio S Gasa A Makita |
spellingShingle |
K Kamio S Gasa A Makita Galactosylceramide containing omega-amino-fatty acids: preparation, characterization, and sulfotransferase acceptor. Journal of Lipid Research |
author_facet |
K Kamio S Gasa A Makita |
author_sort |
K Kamio |
title |
Galactosylceramide containing omega-amino-fatty acids: preparation, characterization, and sulfotransferase acceptor. |
title_short |
Galactosylceramide containing omega-amino-fatty acids: preparation, characterization, and sulfotransferase acceptor. |
title_full |
Galactosylceramide containing omega-amino-fatty acids: preparation, characterization, and sulfotransferase acceptor. |
title_fullStr |
Galactosylceramide containing omega-amino-fatty acids: preparation, characterization, and sulfotransferase acceptor. |
title_full_unstemmed |
Galactosylceramide containing omega-amino-fatty acids: preparation, characterization, and sulfotransferase acceptor. |
title_sort |
galactosylceramide containing omega-amino-fatty acids: preparation, characterization, and sulfotransferase acceptor. |
publisher |
Elsevier |
series |
Journal of Lipid Research |
issn |
0022-2275 |
publishDate |
1992-08-01 |
description |
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%. |
url |
http://www.sciencedirect.com/science/article/pii/S0022227520407758 |
work_keys_str_mv |
AT kkamio galactosylceramidecontainingomegaaminofattyacidspreparationcharacterizationandsulfotransferaseacceptor AT sgasa galactosylceramidecontainingomegaaminofattyacidspreparationcharacterizationandsulfotransferaseacceptor AT amakita galactosylceramidecontainingomegaaminofattyacidspreparationcharacterizationandsulfotransferaseacceptor |
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1721508263944519680 |