Premium
Synthesis of a Biotinated Lipofullerene as a New Type of Transmembrane Anchor
Author(s) -
Braun Martin,
Camps X.,
Vostrowsky Otto,
Hirsch Andreas,
Endreß Emil,
Bayerl Thomas M.,
Birkert Oliver,
Gauglitz Günter
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200004)2000:7<1173::aid-ejoc1173>3.0.co;2-i
Subject(s) - chemistry , malonate , amphiphile , biotin , linker , alkyl , streptavidin , derivative (finance) , stereochemistry , combinatorial chemistry , crystallography , organic chemistry , biochemistry , computer science , economics , financial economics , copolymer , operating system , polymer
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.