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C‐Glycosphingolipids with an exo ‐Methylene Substituent: Stereocontrolled Synthesis and Immunostimulation of Mouse and Human Natural Killer T Lymphocytes
Author(s) -
Liu Zheng,
Courtney Amy N.,
Metelitsa Leonid S.,
Bittman Robert
Publication year - 2012
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201200374
Subject(s) - chemistry , glycolipid , methylene , stereochemistry , aldehyde , substituent , glycosphingolipid , glycoside , ligand (biochemistry) , natural killer t cell , biochemistry , in vitro , receptor , organic chemistry , cytotoxic t cell , catalysis
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.