Chiral vinylphosphonate and phosphonate analogues of the immunosuppressive agent FTY720

Xuequan Lu, Chaode Sun, William J. Valentine, E. Shuyu, Jianxiong Liu, Gabor Tigyi, Robert Bittman

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

The first enantioselective synthesis of chiral isosteric phosphonate analogues of FTY720 is described. One of these analogues, FTY720-(E)- vinylphosphonate (S)-5, but not its R enantiomer, elicited a potent antiapoptotic effect in intestinal epithelial cells, suggesting that it exerts its action via the enantioselective activation of a receptor. (S)-5 failed to activate the sphingosine 1-phosphate type 1 (S1P 1) receptor.

Original languageEnglish (US)
Pages (from-to)3192-3195
Number of pages4
JournalJournal of Organic Chemistry
Volume74
Issue number8
DOIs
StatePublished - Apr 17 2009

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Organophosphonates
Immunosuppressive Agents
Enantiomers
Chemical activation
Fingolimod Hydrochloride
sphingosine 1-phosphate
Epithelial Cells

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Chiral vinylphosphonate and phosphonate analogues of the immunosuppressive agent FTY720. / Lu, Xuequan; Sun, Chaode; Valentine, William J.; Shuyu, E.; Liu, Jianxiong; Tigyi, Gabor; Bittman, Robert.

In: Journal of Organic Chemistry, Vol. 74, No. 8, 17.04.2009, p. 3192-3195.

Research output: Contribution to journalArticle

Lu, Xuequan ; Sun, Chaode ; Valentine, William J. ; Shuyu, E. ; Liu, Jianxiong ; Tigyi, Gabor ; Bittman, Robert. / Chiral vinylphosphonate and phosphonate analogues of the immunosuppressive agent FTY720. In: Journal of Organic Chemistry. 2009 ; Vol. 74, No. 8. pp. 3192-3195.
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