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Molecules 2011, 16(11), 9495-9504; doi:10.3390/molecules16119495
Article

Synthesis of Endohedral Metallofullerene Glycoconjugates by Carbene Addition

1, 2, 2, 1, 2 and 2,*
1 Department of Chemistry, Tokyo Gakugei University, Koganei, Tokyo 184-8501, Japan 2 Life Science Center of Tsukuba Advanced Research Alliance, University of Tsukuba, Tsukuba, Ibaraki 305-8577, Japan
* Author to whom correspondence should be addressed.
Received: 18 October 2011 / Revised: 3 November 2011 / Accepted: 10 November 2011 / Published: 14 November 2011
(This article belongs to the Special Issue Fullerene Chemistry)
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Abstract

Endohedral metallofullerene glycoconjugates were synthesized under mild conditions by carbene addition using appropriate glycosylidene-derived diazirine with La2@Ih-C80. NMR spectroscopic studies revealed that the glycoconjugate consists of two diastereomers of [6,6]-open mono-adducts. The electronic properties were characterized using Vis/NIR absorption spectroscopy and electrochemical measurements. This study demonstrates that glycosylidene carbene is useful to incorporate carbohydrate moieties onto endohedral metallofullerene surfaces.
Keywords: chemical functionalization; La2@Ih-C80; carbohydrate; diazirine; glycoconjugate chemical functionalization; La2@Ih-C80; carbohydrate; diazirine; glycoconjugate
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Yamada, M.; Someya, C.I.; Nakahodo, T.; Maeda, Y.; Tsuchiya, T.; Akasaka, T. Synthesis of Endohedral Metallofullerene Glycoconjugates by Carbene Addition. Molecules 2011, 16, 9495-9504.

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