Title

New multifunctional tags for oligosaccharides

Poster Number

16

Format

Poster Presentation

Abstract/Artist Statement

Carbohydrates play central roles in many cellular processes, and structure-activity studies of carbohydrates begin to receive increasing attention. Solutions to complications during cleanup, separation, and structural characterization of oligosaccharides (OS) have been described in the literature. (a) Partial cleanup of biotin-labeled OS-mixtures prior to chromatography can be accomplished by bioaffinity technology; (b) various UV-active tags can overcome limitations due to the general lack of chromophoric groups in sugars; (c) mass spectrometry and MSn-techniques take a central role in the structural elucidation of OS. In this paper, we present newly-synthesized tags that combine UV-activity, bioaffinity, and ease of chemical introduction into oligosaccharides along with the possibility for isotope-coding and for N-quaternization. The synthesis of the tags, their structural characterization, and the labeling of oligosaccharides is discussed. The tags were synthesized by carbonyl diimidazole coupling of biotin and two benzylic diamines. Oligosaccharides were derivatized with the tags by reductive amination in the presence of NaCNBH3 (or NaCNBD3) and glacial acetic acid. N-Quaternization was carried out in the presence of MeI and NaHCO3. The products were purified by solid-phase extraction (SPE). Electrospray ionization mass spectra and collision-induced dissociation spectra were recorded as well as time-of-flight mass spectra and post-source decay spectra to confirm the identity of the derivatives.

Location

Pacific Geosciences Center

Start Date

24-4-2004 9:00 AM

End Date

24-4-2004 5:00 PM

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Apr 24th, 9:00 AM Apr 24th, 5:00 PM

New multifunctional tags for oligosaccharides

Pacific Geosciences Center

Carbohydrates play central roles in many cellular processes, and structure-activity studies of carbohydrates begin to receive increasing attention. Solutions to complications during cleanup, separation, and structural characterization of oligosaccharides (OS) have been described in the literature. (a) Partial cleanup of biotin-labeled OS-mixtures prior to chromatography can be accomplished by bioaffinity technology; (b) various UV-active tags can overcome limitations due to the general lack of chromophoric groups in sugars; (c) mass spectrometry and MSn-techniques take a central role in the structural elucidation of OS. In this paper, we present newly-synthesized tags that combine UV-activity, bioaffinity, and ease of chemical introduction into oligosaccharides along with the possibility for isotope-coding and for N-quaternization. The synthesis of the tags, their structural characterization, and the labeling of oligosaccharides is discussed. The tags were synthesized by carbonyl diimidazole coupling of biotin and two benzylic diamines. Oligosaccharides were derivatized with the tags by reductive amination in the presence of NaCNBH3 (or NaCNBD3) and glacial acetic acid. N-Quaternization was carried out in the presence of MeI and NaHCO3. The products were purified by solid-phase extraction (SPE). Electrospray ionization mass spectra and collision-induced dissociation spectra were recorded as well as time-of-flight mass spectra and post-source decay spectra to confirm the identity of the derivatives.