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Paper

Org. Biomol. Chem., 2009, 7, 4726 - 4733, DOI: 10.1039/b909556j

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

Katsuhiko Suzuki, Akifumi Tobe, Shin Adachi, Shusaku Daikoku, Yasuko Hasegawa, Yuki Shioiri, Mariko Kobayashi and Osamu Kanie

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 -lactoside with an Erythrina cristagalli lectin, and by visualizing cellular organelles using a more hydrophobic BODIPY-labeled compound.

Graphical abstract image for this article (ID: b909556j)