Analysis ofN-acetylated hexosamine monosaccharides by ferrocenyl boronation and tandem electrospray ionization mass spectrometry

Analysis of neutral isomeric low molecular weight carbohydrates using ferrocenyl boronate derivatization and tandem electrospray mass spectrometry

“…The cell, which is described in previous work,37 is constructed from stainless steel (SS) and quartz tubing and is used in the preformation of ions.…”

“…Using CID of individual (selected) molecular ions in a quadrupole ion‐trap mass spectrometer, each compound can be distinguished by its resultant fragmentation pattern. The reagent, ferrocene boronic acid32,, 33 (F c Bor), forms redox‐active cyclic complexes with five‐ and six‐membered rings with carbohydrates 34–37. The electrospray source in ES‐MS can be considered to be an electrochemical cell,38–41 and as such lends itself to many analyte pre‐ionization schemes.…”

Derivatization of carbohydrates for analysis by chromatography; electrophoresis and mass spectrometry

“…The derivatives were applied to a complex carbohydrate mixture from honey [107]. Ferrocenyl boronates (6) of N-acetylaminohexoses have been differentiated by mass spectral fragmentation after they were formed within the spray of an electrospray instrument [108] and differentiation of isomeric monoand -disaccharides has been achieved by the same technique [109]. It was believed that both five-and six-membered rings were formed.…”

Structural characterization of a series of 10-carbon sugar derivatives by electrospray-ionization MSn mass spectrometry

“…Electrospray ionization (ESI), a soft ionization technique, is a powerful tool for structure elucidation of nonvolatile and thermally labile compounds, especially biological materials [9][10][11][12] and carbohydrate derivatives. [13][14][15][16][17] Many investigations concerning metalion adducts of carbohydrates in ESI-MS experiments have been reported recently, [18][19][20] but to the best of our knowledge, the ESI-MS fragmentation characteristics of higher-carbon amino spiro-sugar derivatives have not been studied. Here, we report the ESI-MS n spectra of a series of such compounds (4a-h, 5a-h, 6a-f, and 7a-f in Scheme 1) to study their fragmentation behavior and establish characteristic fragments suitable for the identification of similar carbohydrates.…”