1 : 1 Adduct Ion Formation of Simple Carbohydrate Derivatives with Cations Using FAB Mass Spectrometry. Comparison of O-Acetyl, N-Butyl, and O-Methyl Modifications

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Abstract
The 1 : 1 adduct ion formation between a series of per-O-acetylated aldopyranoses (family 1) or N-butylated glycosylamines (family 2) and an organic/metallic cation (n-C8H17NH3+/K+ or Li+) has been examined using quantitative FAB mass Spectrometry. The per-O-acetyl modifications dramatically lead to negated selectivity of the carbohydrates toward the cation which has been clearly observed in per-O-methyl modifications. On the other hand, the mono-N-butyl modifications provide a similar selectivity pattern to mono-O-methyl ones. These results are understood on the basis of electronic and structural considerations.

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