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

Jeong Ju Park, Ji Hyung Lee, Subhash C. Ghosh, Gabriel Bricard, Manjunatha M. Venkataswamy, Steven A. Porcelli, Sung Kee Chung

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

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. Crown

Original languageEnglish (US)
Pages (from-to)3906-3909
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume18
Issue number14
DOIs
StatePublished - Jul 15 2008

Fingerprint

Natural Killer T-Cells
Stereoisomerism
Ligands
Structure-Activity Relationship
Bioactivity
Crowns
Cytokines
KRN 7000
Proteins

Keywords

  • α-GalCer
  • KRN7000 stereoisomers
  • NKT cell
  • Phytosphingosine

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Park, J. J., Lee, J. H., Ghosh, S. C., Bricard, G., Venkataswamy, M. M., Porcelli, S. A., & Chung, S. K. (2008). Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand. Bioorganic and Medicinal Chemistry Letters, 18(14), 3906-3909. https://doi.org/10.1016/j.bmcl.2008.06.036

Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand. / Park, Jeong Ju; Lee, Ji Hyung; Ghosh, Subhash C.; Bricard, Gabriel; Venkataswamy, Manjunatha M.; Porcelli, Steven A.; Chung, Sung Kee.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 18, No. 14, 15.07.2008, p. 3906-3909.

Research output: Contribution to journalArticle

Park, Jeong Ju ; Lee, Ji Hyung ; Ghosh, Subhash C. ; Bricard, Gabriel ; Venkataswamy, Manjunatha M. ; Porcelli, Steven A. ; Chung, Sung Kee. / Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand. In: Bioorganic and Medicinal Chemistry Letters. 2008 ; Vol. 18, No. 14. pp. 3906-3909.
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