Synthesis of a Biotinated Lipofullerene as a New Type of Transmembrane Anchor

Autor: Otto Vostrowsky, Emil Endreß, Oliver Birkert, Martin Braun, Thomas M. Bayerl, Günter Gauglitz, Xavier Camps, Andreas Hirsch
Rok vydání: 2000
Předmět:
Zdroj: European Journal of Organic Chemistry. 2000:1173-1181
ISSN: 1099-0690
1434-193X
DOI: 10.1002/1099-0690(200004)2000:7<1173::aid-ejoc1173>3.0.co;2-i
Popis: 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.
Databáze: OpenAIRE
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