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; Osamu Kanie

doi:10.1039/B909556J

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Organic & Biomolecular Chemistry

Issue 22, 2009

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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

Org. Biomol. Chem., 2009, 7, 4726-4733

DOI: 10.1039/B909556J
Received 14 May 2009, Accepted 04 Aug 2009
First published on the web 08 Sep 2009

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Abstract
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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.

Abstract from Mass Spectrometry Bulletin 2010

Carbohydrates, Collision-induced dissociation.

Supplementary Info

Energy-resolved mass spectrometry (ERMS) for compounds 1(α,β) and 8(α,β).¹H-NMR, COSY and HSQC spectra of compounds 1(α,β), 9 and 10. LC-MS chromatograph and MS/MS spectra for compounds 9 and 10
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Katsuhiko Suzuki
Akifumi Tobe
Shin Adachi
Shusaku Daikoku
Yasuko Hasegawa
Yuki Shioiri
Mariko Kobayashi
Osamu Kanie

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Organic & Biomolecular Chemistry

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

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