Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand

In an effort to understand the structure–activity relationships, we have carried out the synthesis of all eight KRN7000 stereoisomers, and their biological activities examined. KRN7000 is an important ligand identified for CD1d protein of APC, and KRN7000/CD1d complex can stimulate NKT cells to rele...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2008-07, Vol.18 (14), p.3906-3909
Main Authors: Park, Jeong-Ju, Lee, Ji Hyung, Ghosh, Subhash C., Bricard, Gabriel, Venkataswamy, Manjunatha M., Porcelli, Steven A., Chung, Sung-Kee
Format: Article
Language:English
Subjects:
Adjuvants, Immunologic - chemical synthesis
Adjuvants, Immunologic - chemistry
Antigens, CD1 - chemistry
Antigens, CD1 - metabolism
Antigens, CD1d
Chemistry, Pharmaceutical - methods
Drug Design
Galactosylceramides - chemical synthesis
Galactosylceramides - chemistry
Humans
Killer Cells, Natural - immunology
Killer Cells, Natural - metabolism
KRN7000 stereoisomers
Ligands
Models, Chemical
NKT cell
Phytosphingosine
Protein Binding
Stereoisomerism
α-GalCer
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Summary:In an effort to understand the structure–activity relationships, we have carried out the synthesis of all eight KRN7000 stereoisomers, and their biological activities examined. KRN7000 is an important ligand identified for CD1d protein of APC, and KRN7000/CD1d complex can stimulate NKT cells to release Th1 and Th2 cytokines. In an effort to understand the structure–activity relationships, we have carried out the synthesis of a complete set of the eight KRN7000 stereoisomers, and their biological activities have been examined.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2008.06.036