Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of oligosaccharides derivatized by reductive amination and N,N-dimethylation

S. Broberg, A. Broberg, Jens Øllgaard Duus

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

Oligosaccharides were derivatized by reductive amination with benzylamine followed by N,N-dimethylation with methyl iodide and analyzed by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOFMS) and MALDI post-source decay (PSD) TOFMS. The resulting derivatives have a positive charge localized to the modified reducing end. The derivatization methodology was tested on maltoheptaose and three different human milk oligosaccharides. The approximate detection limit for the resulting carbohydrate derivatives was determined to be 50 fmol of the derivative loaded onto the target, corresponding to a tenfold increase in sensitivity compared with underivatized oligosaccharides. When the derivatives were analyzed by MALDI-PSD TOFMS the observed fragmentation pattern was dominated by fragment ions retaining the modified reducing terminus, thus simplifying the interpretation of the mass spectral data. Copyright (C) 2000 John Wiley & Sons, Ltd.
Original languageEnglish
JournalRapid Communications in Mass Spectrometry
Volume14
Issue number19
Pages (from-to)1801-1805
ISSN0951-4198
DOIs
Publication statusPublished - 2000
Externally publishedYes

Keywords

  • Amination
  • Carbohydrate Sequence
  • Indicators and Reagents
  • Methylation
  • Molecular Sequence Data
  • Oligosaccharides
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • dyes, reagents, indicators, markers and buffers
  • heptose
  • hexose
  • ion
  • maltose
  • milk
  • oligosaccharide
  • pentose
  • tetrose
  • triose
  • accuracy
  • amination
  • article
  • carbohydrate analysis
  • chemistry
  • derivatization
  • desorption
  • human
  • ionization
  • laser
  • mass fragmentography
  • mass spectrometry
  • methylation
  • molecular genetics
  • reduction
  • surface charge
  • technique
  • Support, Non-U.S. Gov't
  • CHEMISTRY,
  • SPECTROSCOPY
  • PERFORMANCE LIQUID-CHROMATOGRAPHY
  • ACID 2-(DIETHYLAMINO)ETHYL ESTER
  • DESORPTION IONIZATION
  • STRUCTURAL-ANALYSIS
  • DECAY
  • detection limit
  • fragmentation pattern
  • benzylamine 100-46-9 Sigma
  • human milk oligosaccharides
  • maltoheptaose 34620-78-5 Sigma
  • maltohexaose 34620-77-4 Sigma
  • maltopentaose 34620-76-3 Sigma
  • maltotetraose 34612-38-9 Sigma
  • maltotriose 1109-28-0 Sigma
  • methyl iodide 74-88-4 Merck-Schuchardt
  • oligosaccharides
  • 10060, Biochemistry studies - General
  • 10068, Biochemistry studies - Carbohydrates
  • Bruker Reflex III MALDI-TOF mass spectrometer Bruker-Daltonik, laboratory equipment
  • matrix-assisted laser desorption/ionization post-source decay time-of-flight mass spectrometry Spectrum Analysis Techniques, analytical method
  • matrix-assisted laser desorption/ionization time-of-flight mass spectrometry Spectrum Analysis Techniques, analytical method
  • N,N-dimethylation Synthetic Techniques, synthetic method
  • reductive amination Synthetic Techniques, synthetic method
  • Biochemistry and Molecular Biophysics
  • Methods and Techniques

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