In this study maltose, maltotriose and maltotetraose were for the first time, coupled to 4,4′-methylenedianiline (MDA). The aim of this preliminary work was to test the feasibility of oligo- and polysaccharide coupling to MDA and the characterization of the coupling products by high resolution mass spectrometry (MS). (+) nanoESI in combination with a quadrupole time of flight (QTOF) MS in full scan (MS) and MS/MS was optimized first on underivatized maltose, maltotriose and maltotetraose. The optimal screening and sequencing conditions were further applied to the MDA-functionalized oligosaccharides. The obtained results revealed a straightforward MS detection of the functionalized oligomers, high sequence coverage and a fragmentation pathway with the formation of B and Y ions as well as the complementary C and Z ions along with a typical cleavage of the aglycon. We consider that this methodology is fully applicable also to polydisperse mixtures of long chain polysaccharides, which due to the large number of components and their size require a systematic method of development and testing. [...]
A variety of carbohydrates, in particular polysaccharides can be subjected to chemical modification to obtain derivatives with amphiphilic properties, which enable biochemical or biological reactions at the polymer surface. In the present work, a polydisperse maltodextrin mixture of average molecular weight 3000 was coupled with 1,6-hexamethylenediamine (HMD) via reductive amination reaction. Resulting products were characterized by thermal analysis and positive nanoelectrospray quadrupole time-of-flight (Q-TOF) mass spectrometry (MS) and tandem mass spectrometry (MS/MS). Both thermal analysis and MS screening confirmed the formation of the HMD-polysaccharide coupling products. Moreover, HMD-linked polysaccharide chains containing 2 to 26 glucose building blocks were identified by nanoESI Q-TOF MS. MS/MS fragmentation using collision-induced dissociation (CID) at low ion acceleration energies provided strong evidence for HMD-maltodextrin linkage formation and the set of sequence ions diagnostic for the composition and structure of a HMD-linked chain containing 18 glucose residues. [...]
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