01749nas a2200265   4500008004100000022001400041245012200055210006900177260010600246300001400352490000700366520078000373653001401153653001301167653001601180653001101196653001601207100002201223700002701245700002001272700002201292700001901314700002001333856013001353       2014                        eng d  a0968-089600aFlexible, polymer-supported synthesis of sphingosine derivatives provides ceramides with enhanced biological activity0 aFlexible polymersupported synthesis of sphingosine derivatives p  aTHE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLANDbPERGAMON-ELSEVIER SCIENCE LTDcOCT  a5506-55120 v223 a<p>A polymer-supported route for the synthesis of sphingosine derivatives is presented based on the C-acylation of polymeric phosphoranylidene acetates with an Fmoc-protected amino acid. The approach enables the flexible variation of the sphingosine tail through a deprotection-decarboxylation sequence followed by E-selective Wittig olefination cleavage. D-Erythro-sphingosine analogs have been synthesized by diastereoselective reduction of the keto group employing LiAlH(O-tBu)(3) as reducing agent. The effect of ceramides and keto-ceramides on the proliferation of three cancer cell lines HEP G-2, PC-12 and HL-60 was investigated and a ceramide containing an aromatic sphingosine tail was identified as being most active. (C) 2014 Elsevier Ltd. All rights reserved.</p>10aApoptosis10aCeramide10aLipid rafts10aLipids10aSphingosine1 aEl-Dahshan, Adeeb1 aAl-Gharabli, Samer, I.1 aRadetzki, Silke1 aAl-Tel, Taleb, H.1 aKumar, Pradeep1 aRademann, Joerg  uhttps://library.ncl.res.in/content/flexible-polymer-supported-synthesis-sphingosine-derivatives-provides-ceramides-enhanced-0