Electrospray ionization mass spectrometry: a key analytical tool for the characterization of regioselectively derivatized maltooligosaccharides obtained starting from natural β‐cyclodextrin

Abstract

The development of natural cyclodextrins (CDs) for various industrial applications (agroalimentary, cosmetic or pharmaceutical) constitutes a continuous challenge. For the integration of these agricultural plant products in the creation of super-absorbent biodegradable and hypoallergenic materials (water-retaining agents, cosmetic hydrating and texturing, pharmaceutical and horticultural products) to replace synthetic polymers, we have developed chemical methods to access regioselectively C-6-derivatized maltooligosaccharides starting from CDs. These compounds are highly suitable for further chemical modifications and are expected to give access to a new class of polymeric materials with potential applications such as water-retaining agents in the disposable nappies industry. For the structural analysis of carbohydrates, electrospray ionization mass spectrometry (ESI-MS) offers precise results, analytical versatility and very high sensitivity. We report herein the rapid and convenient follow-up of chemical reactions, the purity evaluation of intermediates and final products, and the structural characterization of derivatized maltooligosaccharides, obtained by acidic cleavage (acetolysis) of halogenated and esterified CDs, using ESI-MS in combination with the high-resolution (HRMS) and tandem mass spectrometry (MS/MS) capabilities of a quadrupole orthogonal time-of-flight (Q-TOF) mass spectrometer.

Gas-Phase Fragmentation of Cyclic Oligosaccharides in Tandem Mass Spectrometry

“…ESI MS was used for the characterization of regioselectively derivatized maltooligosaccharides obtained starting from natural β-cyclodextrin [81]. For two intermediates, totally acetylated and totally benzoylated heptakis-(6-deoxy-6-bromo)-β-CD, ESI HR mass spectra were reported, the only ions observed were [M + Na] + .…”