Synthesis of fullerene glycoconjugates via a copper-catalyzed Huisgen cycloaddition reaction.
The synthesis of fullerene-carbohydrate conjugates using a copper-catalyzed [3+2] cycloaddition reaction to facilitate the union of an azido-functionalized sugar and a pentaalkynyl[60]fullerene is straightforward. Thus, fullerenes bearing five oligosaccharides such as Gb3-trisaccharide can be readily accessed. Nanometer-scale molecular architectures presenting as many as 15 sugar moieties in C5-symmetry are readily produced. The cycloaddition reaction proceeds quantitatively under mild conditions without the need to protect the sugar hydroxyl groups.
Isobe
Hiroyuki
H
Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. isobe@mail.tains.tohoku.ac.jp
Cho
Kaimei
K
Solin
Niclas
N
Werz
Daniel B
DB
Seeberger
Peter H
PH
Nakamura
Eiichi
E