Electrospray ionization mass spectrometry: a key analytical tool for the characterization of regioselectively derivatized maltooligosaccharides obtained starting from natural beta-cyclodextrin.
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.
Lesur
David
D
Laboratoire des Glucides, UMR CNRS 6219, Université de Picardie Jules Verne, 33 rue St. Leu, 80039 Amiens Cedex, France.
Gassama
Abdoulaye
A
Moreau
Vincent
V
Djedaïni-Pilard
Florence
F
Brique
Arnaud
A
Pilard
Serge
S
D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis*; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D047392:beta-Cyclodextrins / Q000737:chemistry*
D009844:Oligosaccharides; D047392:beta-Cyclodextrins; C021705:maltooligosaccharides; C031215:betadex