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Issue 22, 2009
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N-Hexyl-4-aminobutyl glycosides for investigating structures and biological functions of carbohydrates

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Abstract

The potential applications of N-hexyl-4-aminobutyl glycosides in the mass spectrometric investigation of glycan structure and in the investigation of glycan functions were studied. Under collision-induced dissociation (CID) conditions, sodiated glycosides carrying N-hexyl-4-aminobutyl groups effectively produced a hemiacetal species (C-ions), which is important in mass-spectrometry-based structural investigation. The usefulness of N-hexyl-4-aminobutyl glycosides in biological analysis was also confirmed by obtaining a binding constant for the binding of dipyrrometheneboron difluoride C3-labeled N-hexyl-4-aminobutyl β-lactoside with an Erythrina cristagalli lectin, and by visualizing cellular organelles using a more hydrophobic BODIPY-labeled compound.

Graphical abstract: N-Hexyl-4-aminobutyl glycosides for investigating structures and biological functions of carbohydrates

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Supplementary files

Article information


Submitted
14 May 2009
Accepted
04 Aug 2009
First published
08 Sep 2009

Org. Biomol. Chem., 2009,7, 4726-4733
Article type
Paper

N-Hexyl-4-aminobutyl glycosides for investigating structures and biological functions of carbohydrates

K. Suzuki, A. Tobe, S. Adachi, S. Daikoku, Y. Hasegawa, Y. Shioiri, M. Kobayashi and O. Kanie, Org. Biomol. Chem., 2009, 7, 4726
DOI: 10.1039/B909556J

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