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Synthesis of Endohedral Metallofullerene Glycoconjugates by Carbene Addition
Department of Chemistry, Tokyo Gakugei University, Koganei, Tokyo 184-8501, Japan
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; in revised form: 3 November 2011 / Accepted: 10 November 2011 / Published: 14 November 2011
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
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MDPI and ACS Style
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.
Yamada M, Someya CI, Nakahodo T, Maeda Y, Tsuchiya T, Akasaka T. Synthesis of Endohedral Metallofullerene Glycoconjugates by Carbene Addition. Molecules. 2011; 16(11):9495-9504.
Yamada, Michio; Someya, Chika I.; Nakahodo, Tsukasa; Maeda, Yutaka; Tsuchiya, Takahiro; Akasaka, Takeshi. 2011. "Synthesis of Endohedral Metallofullerene Glycoconjugates by Carbene Addition." Molecules 16, no. 11: 9495-9504.