Synthesis and characterization of regioselectively monoderivatized maltooligosaccharides through a combination of tandem mass spectrometry and enzymatic hydrolysis studies

Abstract

Recently, we have designed chemical strategies leading to C-6 perfunctionalized linear maltoheptaose derivatives via the acetolysis of persubstituted β-cyclodextrin (β-CD) at the 6-positions. This approach has now been extended to the synthesis of monofunctionalized maltoheptaose derivatives. This report deals with the regioselectivity of the ring opening of monosubstituted β-CD and the use of electrospray ionization tandem mass spectrometry (ESI-MS/MS) to identify the substituted unit. In order to confirm our results, a controlled enzymatic degradation of the resulting derivatives, using the glucoamylase of Aspergillus niger, was performed and monitored by liquid chromatography / electrospray ionization mass spectrometry (LC/ESI-MS).