- Chiral vinylphosphonate and phosphonate analogues of the immunosuppressive agent FTY720.
Chiral vinylphosphonate and phosphonate analogues of the immunosuppressive agent FTY720.
The Journal of organic chemistry (2009-03-20)
Xuequan Lu, Chaode Sun, William J Valentine, E Shuyu, Jianxiong Liu, Gabor Tigyi, Robert Bittman
PMID19296586
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.