C-Glycosphingolipids with an exo-Methylene Substituent: Stereocontrolled Synthesis and Immunostimulation of Mouse and Human Natural Killer T Lymphocytes

Introduction of an exo‐methylene group into the C‐glycoside analogue of KRN7000 was found to afford a new glycosphingolipid ligand with potent agonistic activity for both human and mouse invariant natural killer T lymphocytes. The key synthetic strategy utilized the Nozaki–Hiyama–Kishi reaction to a...

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Bibliographic Details
Published in:Chembiochem : a European journal of chemical biology 2012-08, Vol.13 (12), p.1733-1737
Main Authors: Liu, Zheng, Courtney, Amy N., Metelitsa, Leonid S., Bittman, Robert
Format: Article
Language:English
Subjects:
Adjuvants, Immunologic - chemical synthesis
Adjuvants, Immunologic - pharmacology
Animals
C-glycosides
Cells, Cultured
cytokines
Cytokines - biosynthesis
Cytokines - immunology
Galactosylceramides - chemical synthesis
Galactosylceramides - pharmacology
glycosphingolipids
Glycosphingolipids - chemical synthesis
Glycosphingolipids - pharmacology
Humans
immunostimulants
Lymphocyte Activation - drug effects
Lymphocyte Activation - immunology
Mice
Natural Killer T-Cells - drug effects
Natural Killer T-Cells - immunology
Nozaki-Hiyama-Kishi reaction
Stereoisomerism
Th1-Th2 Balance - drug effects
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Summary:Introduction of an exo‐methylene group into the C‐glycoside analogue of KRN7000 was found to afford a new glycosphingolipid ligand with potent agonistic activity for both human and mouse invariant natural killer T lymphocytes. The key synthetic strategy utilized the Nozaki–Hiyama–Kishi reaction to achieve a high‐yield coupling between an α‐galactosyl aldehyde and a vinyl iodide.
ISSN:1439-4227
1439-7633
DOI:10.1002/cbic.201200374