Abstract
A new immunostimulant, the 4'-epimer of α-C-GalCer, was synthesized from a C2-symmetric dienediol and α-C-allyl galactoside. The intramolecular aziridination and the following reductive ring opening provided the core of the aliphatic amino alcohol with excellent regio- and stereocontrol. The new immunostimulants 3d and 3e gave a better polarized Th1-type cytokine response in murine NKT cells than the benchmarked α-C-GalCer.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Adjuvants, Immunologic / chemical synthesis*
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Adjuvants, Immunologic / chemistry
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Adjuvants, Immunologic / pharmacology
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Animals
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Aziridines / chemistry*
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Cardiac Glycosides
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Cytokines
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Galactosylceramides / chemical synthesis*
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Galactosylceramides / chemistry
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Galactosylceramides / pharmacology*
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Glycosides
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Marine Biology
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Mice
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Mice, Inbred BALB C
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Molecular Structure
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Monosaccharides / chemistry
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Natural Killer T-Cells
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Porifera / chemistry
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Stereoisomerism
Substances
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Adjuvants, Immunologic
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Aziridines
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C-galactosylceramide
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C-glycoside
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Cardiac Glycosides
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Cytokines
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Galactosylceramides
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Glycosides
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Monosaccharides
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alpha-galactosylceramide
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KRN 7000