“Internal Residue Loss”:  Rearrangements Occurring during the Fragmentation of Carbohydrates Derivatized at the Reducing Terminus

Rearrangement reactions involving migration of fucose and, occasionally, other residues have been found in the CID spectra of [M + H]+ and [M + 2H]2+ ions, but not [M + Na]+ ions, generated from several O-linked carbohydrates and milk sugars derivatized at their reducing termini with aromatic amines...

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Bibliographic Details
Published in:Analytical chemistry (Washington) 2002-02, Vol.74 (4), p.734-740
Main Authors: Harvey, David J, Mattu, Taj S, Wormald, Mark R, Royle, Louise, Dwek, Raymond A, Rudd, Pauline M
Format: Article
Language:English
Subjects:
Amines - chemistry
Analytical, structural and metabolic biochemistry
Animals
Biological and medical sciences
Carbohydrate Sequence
Carbohydrates
Carbohydrates - chemistry
Chemistry
Fucose - analysis
Fundamental and applied biological sciences. Psychology
Milk - chemistry
Miscellaneous
Models, Molecular
Molecular Sequence Data
Other biological molecules
Oxidation-Reduction
Spectrometry, Mass, Electrospray Ionization
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Summary:Rearrangement reactions involving migration of fucose and, occasionally, other residues have been found in the CID spectra of [M + H]+ and [M + 2H]2+ ions, but not [M + Na]+ ions, generated from several O-linked carbohydrates and milk sugars derivatized at their reducing termini with aromatic amines such as 2-aminobenzamide. Such rearrangements, which are similar to those reported by other investigators from several underivatized carbohydrates and glycosides, cause an apparent loss of sugar residues from within a carbohydrate chain and can produce ambiguous results during spectral interpretation. A mechanism, involving initial protonation of the amine nitrogen atom of the derivative, is proposed to account for the formation of the observed ions.
ISSN:0003-2700
1520-6882
DOI:10.1021/ac0109321