Structural identification of new glycolipids based on cyclodextrin using high-resolution positive and negative electrospray ionization mass spectrometry

Abstract

In the continuing challenge to increase the performance of cyclodextrins (CDs) for various applications, new phospholipidyl-cyclodextrin derivatives showing improved self-organization properties in water have been synthesized, as new carriers for drug vectorization, starting from natural beta-cyclodextrin. Due to the important chemical modifications of the original cyclic oligosaccharide molecules, simple nuclear magnetic resonance (NMR) experiments do not easily lead to both an unambiguous assignment of the structures and to a rapid evaluation of the purity of the final products. However, positive and negative ion electrospray ionization (ESI-MS) in combination with accurate mass measurements and tandem mass spectrometry (MS/MS) led to the positive structural identification of the first series of these new amphiphilic compounds.