Sugar balls: Synthesis and supramolecular assembly of [60]fullerene glycoconjugates
Kato H, Boettcher C, Hirsch A (2007)
Publication Type: Journal article, Original article
Publication year: 2007
Journal
Original Authors: Kato H., Böttcher C., Hirsch A.
Publisher: Wiley-VCH Verlag
Pages Range: 2659-2666
Journal Issue: 16
Abstract
The synthesis and characterization of fully deprotected C glycoconjugates 4 and 17 is reported. Bis(α-D-mannopyranosyl)malonamide 4 was obtained by using nucleophilic cyclopropanation chemistry, which in general is a very versatile method for fullerene functionalization. Fullerene sugar 17 contains two dendritic α-D-mannopyranosides that are connected through two adjacent imino bridges to the all-carbon framework. In this adduct-type of C , which represents a 1,9-dihydro-1a-aza-1(2)a-homo(C -I )[5,6]fullerene derivative, the entire 60-π-electron system of the fullerene core is retained. This architecture allows the basic cleavage of the acetyl protection groups of precursor adduct 16 without destruction of the core structure of the fullerene sugar. Dendritic glycoconjugate 17 containing six deprotected sugar building blocks is very soluble in water. The amphiphilic nature of 17 with its cone-shaped structure forces the formation of small supramolecular aggregates in aqueous solutions to shield the hydrophobic fullerene units from the water subphase. DOSY NMR spectroscopy and TEM investigation reveal micellar sugar balls with an extremely narrow size distribution of around 4 nm. © Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
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APA:
Kato, H., Boettcher, C., & Hirsch, A. (2007). Sugar balls: Synthesis and supramolecular assembly of [60]fullerene glycoconjugates. European Journal of Organic Chemistry, 16, 2659-2666. https://dx.doi.org/10.1002/ejoc.200700179
MLA:
Kato, Haruhito, Christoph Boettcher, and Andreas Hirsch. "Sugar balls: Synthesis and supramolecular assembly of [60]fullerene glycoconjugates." European Journal of Organic Chemistry 16 (2007): 2659-2666.
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