title: 2-picoline-borane: a non-toxic reducing agent for oligosaccharide labeling by reductive amination.
abstract: Analysis of N-glycans is often performed by LC coupled to fluorescence detection. The N-glycans are usually labeled by reductive amination with a fluorophore containing a primary amine to allow fluorescence detection. Moreover, many of the commonly applied labels also allow improved mass spectrometric detection of oligosaccharides. For reductive amination, the amine group of the label reacts with the reducing-end aldehyde group of the oligosaccharide to form a Schiff base, which is reduced to a secondary amine. Here, we propose the use of 2-picoline-borane as the reducing agent, as a non-toxic alternative to the extensively used, but toxic sodium cyanoborohydride. Using dextran oligosaccharides and plasma N-glycans, we demonstrate similar labeling efficacies for 2-picoline-borane and sodium cyanoborohydride. Therefore, 2-picoline-borane is a non-toxic alternative to sodium cyanoborohydride for the labeling of oligosaccharides.
authors.affiliation: Department of Parasitology, Leiden University Medical Center, Leiden, The Netherlands. l.r.ruhaak@lumc.nl
authors.forename: L Renee
authors.initials: LR
authors.lastname: Ruhaak
authors.forename: Evelyne
authors.initials: E
authors.lastname: Steenvoorden
authors.forename: Carolien A M
authors.initials: CA
authors.lastname: Koeleman
authors.forename: André M
authors.initials: AM
authors.lastname: Deelder
authors.forename: Manfred
authors.initials: M
authors.lastname: Wuhrer
mesh_terms: D005453:Fluorescence; D006023:Glycoproteins / Q000737:chemistry; D009844:Oligosaccharides / Q000737:chemistry*; D010847:Picolines / Q000737:chemistry; D040901:Proteomics / Q000379:methods*; D019163:Reducing Agents / Q000737:chemistry*
chemical_list: D006023:Glycoproteins; D009844:Oligosaccharides; D010847:Picolines; D019163:Reducing Agents