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Flexible, polymer-supported synthesis of sphingosine derivatives provides ceramides with enhanced biological activity

Item Type:Article
Title:Flexible, polymer-supported synthesis of sphingosine derivatives provides ceramides with enhanced biological activity
Creators Name:El-Dahshan, A. and Al-Gharabli, S.I. and Radetzki, S. and Al-Tel, T.H. and Kumar, P. and Rademann, J.
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.
Keywords:Lipids, Sphingosine, Ceramide, Apoptosis, Lipid Rafts
Source:Bioorganic and Medicinal Chemistry
ISSN:0968-0896
Publisher:Elsevier / Pergamon (U.K.)
Volume:22
Number:19
Page Range:5506-5512
Date:1 October 2014
Official Publication:https://doi.org/10.1016/j.bmc.2014.07.024
PubMed:View item in PubMed

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