Fullerenoid lipids: first synthesis of structured triacylglycerols containing an Aza-[60]fullerene unit.

Abstract:

: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 bromo-triacylglycerols (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 bromo-triacylglycerols with sodium azide. The resulting azido-triacylglycerols were then reacted with [60]fullerene to give the requisite aza-fullerenoid triacylglycerol of the type ABA or AAB (45-62% yield based on the amount of [60]fullerene 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 deltaC 133-148 (carbon shifts of Sp2 carbons of the cage) in the 13C nuclear magnetic resonance spectra. The spectroscopic and mass spectrometric properties of these novel fullerenoid triacylglycerols are reported.

journal_name

Lipids

journal_title

Lipids

authors

Jie MS,Cheung SW,Ho JC

doi

10.1007/s11745-001-0769-6

subject

Has Abstract

pub_date

2001-06-01 00:00:00

pages

649-54

issue

6

eissn

0024-4201

issn

1558-9307

journal_volume

36

pub_type

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