"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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书目详细资料
Main Authors: Harvey, D, Mattu, T, Wormald, M, Royle, L, Dwek, R, Rudd, P
格式: Journal article
语言:English
出版: 2002
实物特征
总结: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.