Synthesis of a biotinated lipofullerene as a new type of transmembrane anchor

Braun M, Camps X, Vostrowsky O, Hirsch A, Endreß E, Bayerl T, Birkert O, Gauglitz G (2000)


Publication Type: Journal article, Original article

Publication year: 2000

Journal

Original Authors: Braun M., Camps X., Vostrowsky O., Hirsch A., Endress E., Bayerl T.M., Birkert O., Gauglitz G.

Publisher: Wiley-VCH Verlag

Pages Range: 1173-1181

Journal Issue: 7

URI: https://www.scopus.com/record/display.uri?eid=2-s2.0-0034014227&origin=inward

Abstract

As a prototype for a new class of lipid membrane components, the lipophilic fullerene derivative (so-called lipofullerene) 1 was synthesized and characterized. This mixed [1:5]hexakisadduct consists of ten long alkyl chains within five didodecyl malonate addends and a linker malonate carrying a (+)-biotin unit as part of an amphiphilic spacer. The malonates are attached to the fullerene core in an octahedral addition pattern, which was achieved by two successive cyclopropanation sequences with the functional precursor malonate 8 and dodecyl malonate 10. The final step of the synthesis of 1 was the attachment of activated biotin 5 with the deprotected precursor 11. Binding experiments followed by reflectometric interference spectroscopy [RIfS] proved the capability of 1 to bind specifically the protein streptavidin (SA) through the biotin unit. The amphiphilic behavior of 1 was demonstrated by Langmuir Blodgett (LB) film investigations.

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How to cite

APA:

Braun, M., Camps, X., Vostrowsky, O., Hirsch, A., Endreß, E., Bayerl, T.,... Gauglitz, G. (2000). Synthesis of a biotinated lipofullerene as a new type of transmembrane anchor. European Journal of Organic Chemistry, 7, 1173-1181.

MLA:

Braun, Martin, et al. "Synthesis of a biotinated lipofullerene as a new type of transmembrane anchor." European Journal of Organic Chemistry 7 (2000): 1173-1181.

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