2-picoline-borane: a non-toxic reducing agent for oligosaccharide labeling by reductive amination

Area of Science:

• Analytical Chemistry
• Biochemistry
• Glycobiology

Background:

• N-glycan analysis is crucial for understanding biological processes.
• Liquid chromatography (LC) coupled with fluorescence detection is a common method for N-glycan analysis.
• Reductive amination is typically used to label N-glycans with fluorophores for detection.

Purpose of the Study:

• To introduce 2-picoline-borane as a non-toxic reducing agent for N-glycan labeling.
• To evaluate the efficacy of 2-picoline-borane as an alternative to sodium cyanoborohydride.
• To demonstrate the utility of 2-picoline-borane for both fluorescence and mass spectrometric detection of N-glycans.

Main Methods:

• Reductive amination of N-glycans using fluorescent labels.
• Comparison of 2-picoline-borane with sodium cyanoborohydride as reducing agents.
• Analysis of labeled dextran oligosaccharides and plasma N-glycans using LC.

Main Results:

• 2-picoline-borane demonstrated comparable labeling efficiencies to sodium cyanoborohydride.
• The proposed method allows for fluorescence and mass spectrometric detection of N-glycans.
• No significant differences in labeling efficacy were observed between the two reducing agents.

Conclusions:

• 2-picoline-borane is a safe and effective non-toxic alternative to sodium cyanoborohydride for N-glycan labeling.
• This finding facilitates safer and more accessible N-glycan analysis.
• The method supports sensitive detection of N-glycans in biological samples.