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

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Item Type:	Article
Title:	Flexible, polymer-supported synthesis of sphingosine derivatives provides ceramides with enhanced biological activity
Creators:	El-Dahshan, A., Al-Gharabli, S.I., Radetzki, S. ORCID: https://orcid.org/0000-0003-2688-2868, Al-Tel, T.H., Kumar, P. and Rademann, J. ORCID: https://orcid.org/0000-0001-6678-3165
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
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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