TY - JOUR
T1 - 2-Picoline-borane
T2 - A non-toxic reducing agent for oligosaccharide labeling by reductive amination
AU - Ruhaak, L. Renee
AU - Steenvoorden, Evelyne
AU - Koeleman, Carolien A.M.
AU - Deelder, André M.
AU - Wuhrer, Manfred
N1 - Copyright:
Copyright 2010 Elsevier B.V., All rights reserved.
PY - 2010/6
Y1 - 2010/6
N2 - 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.
AB - 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.
KW - Fluorescent labeling
KW - Glycoproteomics
KW - Oligosaccharide analysis
KW - Reductive amination
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U2 - 10.1002/pmic.200900804
DO - 10.1002/pmic.200900804
M3 - Article
C2 - 20391534
AN - SCOPUS:77953853129
SN - 1615-9853
VL - 10
SP - 2330
EP - 2336
JO - Proteomics
JF - Proteomics
IS - 12
ER -