Fullerenoid lipids: First synthesis of structured triacylglycerols containing an aza-[60]fullerence unit

Autor: Marcel S. F. Lie Ken Jie, Sunny W. H. Cheung, Janette C. M. Ho
Rok vydání: 2001
Předmět:
Zdroj: Lipids. 36:649-654
ISSN: 1558-9307
0024-4201
DOI: 10.1007/s11745-001-0769-6
Popis: Some 1,2- and 1,3-diacyl glycerols (with acyl groups as stearyl, oleyl, linoleyl, or stearolyl) were synthesized by conventional methods. The diacyl glycerols were esterified with 6-bromo-hexanoic acid to give the corresponding bromotriacylglycerols (of the type AAB and ABA containing a bromo group at the distal part of the hexanoate chain). The bromo function was transformed to an azide group by reaction of the bromotriacylglycerols with sodium azide. The resulting azido-triacylglycerols were then reacted with [60]fullerence to give the requisite aza-fullerenoid triacylglycerol of the type ABA or AAB (45–62% yield based on the amount of [60]fullerence reacted). The nitrogen atom attached to the carbon cage formed a “[5,6]-open” type aza substructure, which was confirmed by the appearance of 31–32 signals in the region of δC 133–148 (carbon shifts of sp 2 carbons of the cage) in the 13C nuclear magnetic resonance spectra. The spectroscopic and mass spectrometric properties of these novel fullerenoid triacylglycerols are reported.
Databáze: OpenAIRE
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