title: Chiral vinylphosphonate and phosphonate analogues of the immunosuppressive agent FTY720.
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.
authors.affiliation: Department of Chemistry and Biochemistry, Queens College of The City University of New York, Flushing, New York 11367-1597, USA.
authors.forename: Xuequan
authors.initials: X
authors.lastname: Lu
authors.forename: Chaode
authors.initials: C
authors.lastname: Sun
authors.forename: William J
authors.initials: WJ
authors.lastname: Valentine
authors.forename: E
authors.initials: E
authors.lastname: Shuyu
authors.forename: Jianxiong
authors.initials: J
authors.lastname: Liu
authors.forename: Gabor
authors.initials: G
authors.lastname: Tigyi
authors.forename: Robert
authors.initials: R
authors.lastname: Bittman
mesh_terms: D000818:Animals; D002478:Cells, Cultured; D000068876:Fingolimod Hydrochloride; D006801:Humans; D007166:Immunosuppressive Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D007413:Intestinal Mucosa / Q000187:drug effects; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D011409:Propylene Glycols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D049349:Receptors, Lysosphingolipid / Q000187:drug effects; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: C542743:((E)-3-amino-5-(4-heptylphenyl)-3-(hydroxymethyl)pent-1-enyl)phosphonic acid; D007166:Immunosuppressive Agents; D063065:Organophosphonates; D011409:Propylene Glycols; D049349:Receptors, Lysosphingolipid; D014753:Vinyl Compounds; C433467:vinylphosphonic acid; D000068876:Fingolimod Hydrochloride; D013110:Sphingosine