Flexible,polymer-supported synthesis of sphingosine derivatives provides ceramides with enhanced biological activity |
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| Affiliation: | 1. Peter Grünberg Institut, Forschungszentrum Jülich GmbH, 52425 Jülich, Germany;2. International Center for Quantum Materials, Peking University, Beijing 100871, People''s Republic of China;3. Institute of Physics, Chinese Academy of Sciences, Beijing 100080, People''s Republic of China;1. Centro Brasileiro de Pesquisas Físicas, Rio de Janeiro 22290-180, RJ, Brazil;2. Facultad de Ciencias Físicas, Universidad Nacional Mayor de San Marcos, Lima, P.O.B. 14-149, Lima 14, Peru;3. Departamento de Física, Universidade Federal do Espírito Santo, Vitória 29075-910, ES, Brazil;4. Institut für Physik der Kondensierten Materie, Technische Universität Braunschweig, 38106 Braunschweig, Germany |
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| Abstract: | 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. |
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| Keywords: | Lipids Sphingosine Ceramide Apoptosis Lipid rafts |
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