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

Liu Zheng | Zendy; Courtney Amy N. | Zendy; Metelitsa Leonid S. | Zendy; Bittman Robert | Zendy

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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.

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