Reductive amination of carbohydrates using NaBH(OAc)3

An improved protocol for reductive amination of carbohydrates is developed. This derivatization facilitates the detection of oligosaccharides in HPLC-UV and mass spectrometric applications by enhancing the signal of the carbohydrates. In this study, reductive amination was achieved using NaBH(OAc)3....

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Bibliographic Details
Published in:Analytical and bioanalytical chemistry 2005-03, Vol.381 (6), p.1130-1137
Main Authors: Dalpathado, Dilusha S, Jiang, Hui, Kater, Marcus A, Desaire, Heather
Format: Article
Language:English
Subjects:
Acetates - chemistry
Amination
Borohydrides - chemistry
Borohydrides - pharmacology
Carbohydrates - chemistry
Chromatography, High Pressure Liquid
Oligosaccharides - analysis
Oxidation-Reduction
Reducing Agents - pharmacology
Reproducibility of Results
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization - methods
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Summary:An improved protocol for reductive amination of carbohydrates is developed. This derivatization facilitates the detection of oligosaccharides in HPLC-UV and mass spectrometric applications by enhancing the signal of the carbohydrates. In this study, reductive amination was achieved using NaBH(OAc)3. This reducing agent is an attractive alternative to the toxic, but extensively used reducing agent, NaBH3CN. Several types of carbohydrates were successfully derivatized using NaBH(OAc)3, and the results obtained from this protocol were compared with those obtained with NaBH(OAc)3. Both reducing agents were equally effective in side-by-side analysis. Two purification strategies (purification by zip-tip and HPLC) were implemented and the instrumental limit of detection of each method was compared. The detection limit was approximately 1,000 times lower when the purification was done using HPLC, compared to using the zip-tip. Since the derivatization by-products in this protocol are not toxic, MS analysis also could also be performed directly, without purification. The MS/MS data of derivatized and underivatized oligosaccharides were acquired as well. The derivatized oligosaccharides produce more easily interpretable product ions than underivatized oligosaccharides.
ISSN:1618-2642
1618-2650
DOI:10.1007/s00216-004-3028-9