Lipid-rafts are membrane microdomains particularly enriched in glycosphingolipids (GSLs) involved in the information transduction process across the membrane. The great interest for such domains is due to the observation that some membrane associated proteins are highly concentrated in lipid rafts, even if the overall protein content of these membrane areas is very low. It has been assumed that the trapping of certain proteins in lipid rafts might be somehow functional to their biological role, i.e. their involvement in signal transduction processes. GSL-protein interactions can be investigated by cell photolabelling experiments using radioactive photoactivable GSLs, which yield, when illuminated, a very reactive intermediate that covalently binds to the molecules in the environment, i.e. proteins. In this context, we have designed a fatty acid probe with two nitrophenylazide photoactivable groups, one at position 2 and the other at the end of the acyl chain. The conjugation of the fatty acid to a radioactive glycosphingolipid generates a species to be used for photolabelling experiments allowing the simultaneous identification of the proteins belonging to the cytoplasmatic and the extracellular leaflets of the membrane. Herein we describe a general synthetic strategy to obtain not commercially available α,ω-diamino acids, the synthetic precursors of the labelled fatty acids, which we have applied to the synthesis of a C-18 derivative. Furthermore, it will be described the preparation of a photolabelled radioactive GSL as a case study.

Photoactivable probes for the study of glycosphingolipid-protein interactions in lipid-rich membrane domains / G. Brasile, F. Compostella, L. Mauri, F. Ronchetti, S. Sonnino. - In: THE FEBS JOURNAL. - ISSN 1742-464X. - 278:suppl. 1(2011 Jun), pp. 417-417. ((Intervento presentato al 36. convegno FEBS congress : biochemistry for tomorrow's medicine tenutosi a Torino nel 2011.

Photoactivable probes for the study of glycosphingolipid-protein interactions in lipid-rich membrane domains

G. Brasile
Primo
;
F. Compostella
Secondo
;
L. Mauri;F. Ronchetti
Penultimo
;
S. Sonnino
Ultimo
2011

Abstract

Lipid-rafts are membrane microdomains particularly enriched in glycosphingolipids (GSLs) involved in the information transduction process across the membrane. The great interest for such domains is due to the observation that some membrane associated proteins are highly concentrated in lipid rafts, even if the overall protein content of these membrane areas is very low. It has been assumed that the trapping of certain proteins in lipid rafts might be somehow functional to their biological role, i.e. their involvement in signal transduction processes. GSL-protein interactions can be investigated by cell photolabelling experiments using radioactive photoactivable GSLs, which yield, when illuminated, a very reactive intermediate that covalently binds to the molecules in the environment, i.e. proteins. In this context, we have designed a fatty acid probe with two nitrophenylazide photoactivable groups, one at position 2 and the other at the end of the acyl chain. The conjugation of the fatty acid to a radioactive glycosphingolipid generates a species to be used for photolabelling experiments allowing the simultaneous identification of the proteins belonging to the cytoplasmatic and the extracellular leaflets of the membrane. Herein we describe a general synthetic strategy to obtain not commercially available α,ω-diamino acids, the synthetic precursors of the labelled fatty acids, which we have applied to the synthesis of a C-18 derivative. Furthermore, it will be described the preparation of a photolabelled radioactive GSL as a case study.
Settore BIO/10 - Biochimica
giu-2011
Federation of European Biochemical Societies (FEBS)
Italian Society of Biochemistry and Molecular Biology (SIB)
Università di Torino
http://onlinelibrary.wiley.com/doi/10.1111/j.1742-4658.2011.08137.x/pdf
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/159478
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